Dorzolamide supplier | CasNO.120279-96-1

Name
Dorzolamide
EINECS 1533716-785-6
CAS No. 120279-96-1
Article Data6
CAS DataBase
Density 1.53 g/cm³
Solubility
Melting Point
Formula C₁₀H₁₆N₂O₄S₃
Boiling Point 575.8 °C at 760 mmHg
Molecular Weight 324.446
Flash Point 302 °C
Transport Information
Appearance White or almost white crystalline powder
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Dorzolamide HCl;4H-Thieno[2,3-b]thiopyran-2-sulfonamide,4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-;4S,6S-Dorzolamide;
PSA
LogP

Synthetic route

: 147200-03-1
(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
With zinc(II) tetrahydroborate In methanol at 90℃; for 3h; Temperature; Solvent; Green chemistry;	90%

: N-ethyl-N-[(4S,6S)-6-methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl]acetamide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
With hydrogenchloride; water In methanol for 72h; Heating / reflux;	66%

: 4-(acetylamino)-5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
With dimethylsulfide borane complex; sulfuric acid 1) THF, r.t.; Yield given. Multistep reaction;

: 147086-79-1
(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 4: 89.6 percent / H2SO4 / 20 - 25 °C 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 7 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: H2SO4 / -5 °C 4: H2SO4 / -5 °C 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 6 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 147086-80-4
5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 3: 89.6 percent / H2SO4 / 20 - 25 °C 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 6 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: H2SO4 / -5 °C 3: H2SO4 / -5 °C 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 5 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 133359-80-5
(S)-3-(thien-2-ylthio)butyric acid

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 5: 89.6 percent / H2SO4 / 20 - 25 °C 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 8 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: H2SO4 / -5 °C 5: H2SO4 / -5 °C 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 7 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 147086-84-8
(S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / -5 °C 2: chlorosulfonic acid / 12 h / 50 °C 3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 133359-79-2
methyl (S)-3-(thiophen-2-ylthio)butyrate

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 6: 89.6 percent / H2SO4 / 20 - 25 °C 7: chlorosulfonic acid / 12 h / 50 °C 8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 9 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: H2SO4 / -5 °C 6: H2SO4 / -5 °C 7: chlorosulfonic acid / 12 h / 50 °C 8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 8 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 1034290-08-8
5,6-dihydro-(R,S)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 2: 89.6 percent / H2SO4 / 20 - 25 °C 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 5 steps 1: H2SO4 / -5 °C 2: H2SO4 / -5 °C 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme
Multi-step reaction with 4 steps 1: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 2: chlorosulfonic acid / 12 h / 50 °C 3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 4-(acetylamino)-5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonyl chloride 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 2: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-4-yl)acetamide 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 12 h / 50 °C 2: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 3: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 5,6-dihydro-(R,S)-4-acetoxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide

: 120279-96-1
dorzolamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89.6 percent / H2SO4 / 20 - 25 °C 2: chlorosulfonic acid / 12 h / 50 °C 3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme

: 120279-96-1
dorzolamide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate pH=1;	95%
With hydrogenchloride In water; dimethyl sulfoxide at 5 - 10℃; for 3h; pH=1.0;

: 6217-54-5
docosahexaenoic acid

: 120279-96-1
dorzolamide

: (4S,6S)-4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ*6*-thieno[2,3-b]thiopyran-2-sulfonic acid ((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)amide

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: docosahexaenoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	95%

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 120279-96-1
dorzolamide

: (E)-N'-{[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}-N,N-dimethylmethanimidamide

Conditions

Conditions	Yield
With trimethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;	95%

: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[ (2S)-2-{[ (2S)-2-{[(2S)-2-{[(2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[ (2S)-2-{[ (2S)-2-{[(2S)-2-{[(2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	84%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[ (2S)-2-{[ (2S)-2-{[(2S)-2-{[(2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;

84%

: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere; Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	84%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere;
Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;

84%

: 4530-20-5
BOC-glycine

: 120279-96-1
dorzolamide

: tert‐butyl N‐[({[(2S,4S)‐4‐(ethylamino)‐2‐methyl‐1,1‐dioxo‐2H,3H,4H‐1λ6‐thieno[2,3‐b]thiopyran‐6‐yl]sulfonyl}carbamoyl)methyl]carbamate

Conditions

Conditions	Yield
Stage #1: dorzolamide With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: BOC-glycine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	82%

: 120279-96-1
dorzolamide

: 58479-61-1
tert-butylchlorodiphenylsilane

: (2S,4S)-N-(tert-butyldiphenylsilyl)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-sulfonamide

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 30℃; for 2h;	76%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 3h; Inert atmosphere;	49%

: 2‐(2‐{[4‐(tert‐butoxy)‐4‐oxobutanoyl]oxy}‐N‐methylacetamido)acetic acid

: 120279-96-1
dorzolamide

: 1-tert-butyl 4-{[({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)methyl](methyl)carbamoyl}methyl butanedioate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 4h; Inert atmosphere;	74%

: {[(acetyloxy)acetyl](methyl)amino}acetic acid

: 120279-96-1
dorzolamide

: {[({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)methy](methyl)carbamoyl}methyl acetate

Conditions

Conditions	Yield
Stage #1: dorzolamide With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: {[(acetyloxy)acetyl](methyl)amino}acetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	72.7%

: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	72%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-[(tert butyldiphenylsilyl)oxy]propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;

72%

: 120279-96-1
dorzolamide

: 125941-75-5
(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid

: (2S)-2-[(tert-butyldiphenylsilyl)oxy]-N-{[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}propanamide

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	68%

: (S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (S)-1-((S)-1-carboxyethoxycarbonyl)ethyl ester

: 120279-96-1
dorzolamide

: (2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (S)-1-((S)-1-carboxyethoxycarbonyl)ethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	68%

: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-[(S)-1-((S)-1-carboxy-ethoxycarbonyl)-ethoxycarbonyl]-ethyl ester

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-[(S)-1-((S)-1-carboxy-ethoxycarbonyl)-ethoxycarbonyl]-ethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	65%

: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-[(S)-1-((S)-1-carboxy-ethoxycarbonyl)-ethoxycarbonyl]-ethyl ester

: 120279-96-1
dorzolamide

: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-{(S)-1-[(S)-2-((4S,6S)-4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ-6-thieno[2,3-b]thiopyran-2-sulfonylamino)-1-methyl-2-oxo-ethoxycarbonyl]ethoxycarbonyl}ethyl ether

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	65%

: (S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxycarbonyl]ethoxycarbonyl}ethyl ester

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-[(tert-butyldiphenylsilyl)oxy]propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxycarbonyl]ethoxycarbonyl}ethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	63%

: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-carboxy-ethyl ester

: 120279-96-1
dorzolamide

: (S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (S)-2-((4S,6S)-4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ*6*-thieno[2,3-b]thiopyran-2-sulfonylamino)-1-methyl-2-oxoethyl ester

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-(tert-butyl-diphenyl-silanyloxy)-propionic acid (S)-1-carboxy-ethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	60%

: 120279-96-1
dorzolamide

: 13831-31-7
Acetoxyacetyl chloride

: {[(2S,4S)-6-{[2-(acetyloxy)acetamido]sulfonyl}-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-4-yl](ethyl)carbamoyl}methyl acetate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: Acetoxyacetyl chloride With dmap In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	59.6%

: 22128-62-7
carbonochloridic acid, chloromethyl ester

: 120279-96-1
dorzolamide

: chloromethyl ethyl[(4S,6S)-6-methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl]carbamate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: carbonochloridic acid, chloromethyl ester In dichloromethane at 0 - 30℃; for 1h; Temperature; Inert atmosphere;	57%
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: carbonochloridic acid, chloromethyl ester In dichloromethane at 0 - 5℃; for 1h;

: 2-(2-{[4-(tert-butoxy)-4-oxobutanoyl]oxy}acetamido)acetic acid

: 120279-96-1
dorzolamide

: 1-tert-butyl 4-{[({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)methyl]carbamoyl}methyl butanedioate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 4h; Inert atmosphere;	50%

: 4-{[(acetyloxy)acetyl]oxy}butanoic acid

: 120279-96-1
dorzolamide

: 3-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-6-sulfamoyl-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)propyl 2-(acetyloxy)acetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	48%

: [({[(acetyloxy)acetyl]oxy}acetyl)(methyl)amino]acetic acid

: 120279-96-1
dorzolamide

: {[({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)methyl](methyl)carbamoyl}methyl 2-(acetyloxy)acetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;	45.1%

: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy} propanoic acid

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-(acetyloxy)propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy} propanoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;	42%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy} propanoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;

42%

: octadecanoic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxy carbonyl]ethoxycarbonyl}ethyl ester

: 120279-96-1
dorzolamide

: octadecanoic acid (S)-1-((S)-1-{(S)-1-[(S)-2-(4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ*6*-thieno[2,3-b]thiopyran-2-sulfonylamino)-1-methyl-2-oxoethoxycarbonyl]ethoxycarbonyl}ethoxycarbonyl)ethyl ester

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: octadecanoic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxy carbonyl]ethoxycarbonyl}ethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	41%

: 108-24-7
acetic anhydride

: 120279-96-1
dorzolamide

: N-ethyl-N-[(4S,6S)-6-methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl]acetamide

Conditions

Conditions	Yield
Stage #1: dorzolamide With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetic anhydride In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;	40%

: (S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid

: 120279-96-1
dorzolamide

: (2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl (2S)-2-(acetyloxy)propanoate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h;	38%

: (2S)-2-{[(2S)-2-[(4-{[(3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl]oxy}-4-oxobutanoyl)oxy]propanoyl]oxy}propanoic acid

: 120279-96-1
dorzolamide

: (3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl (2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl butanedioate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2S)-2-{[(2S)-2-[(4-{[(3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl]oxy}-4-oxobutanoyl)oxy]propanoyl]oxy}propanoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h;	38%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (2S)-2-{[(2S)-2-[(4-{[(3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl]oxy}-4-oxobutanoyl)oxy]propanoyl]oxy}propanoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h;

38%

: succinic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxycarbonyl]ethoxycarbonyl}ethyl ester 3-[1-[4-(2-diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl ester

: 120279-96-1
dorzolamide

: (3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl (2S)-1-{[(2S)-1-{[(2S)-1-[(1S)-1-({[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}carbamoyl)ethoxy]-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl]oxy}-1-oxopropan-2-yl butanedioate

Conditions

Conditions	Yield
Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: succinic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxycarbonyl]ethoxycarbonyl}ethyl ester 3-[1-[4-(2-diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl ester With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h;	38%

Yield

Stage #1: dorzolamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: succinic acid (S)-1-{(S)-1-[(S)-1-((S)-1-carboxyethoxycarbonyl)ethoxycarbonyl]ethoxycarbonyl}ethyl ester 3-[1-[4-(2-diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl ester With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h;

38%

: 2-{2-[3-(butylamino)-4-phenoxy-5-sulfamoylbenzoyloxy]-N-methylacetamido}acetic acid

: 120279-96-1
dorzolamide

: C32H41N5O11S4

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 16h;	38%

Dorzolamide Chemical Properties

IUPAC Name: (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[5,4-b]thiopyran-2-sulfonamide
Synonyms of Dorzolamide (CAS NO.120279-96-1) : 4S,6S-Dorzolamide ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S,6S)- ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-
InChI: InChI=1/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
CAS NO:120279-96-1
Molecular Formula:C₁₀H₁₆N₂O₄S₃
Molecular Weight :324.44
Molecular Structure :
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 119.76 Å²
Index of Refraction: 1.634
Molar Refractivity: 75.48 cm³
Molar Volume: 211 cm³
Surface Tension: 69.4 dyne/cm
Density: 1.53 g/cm³
Flash Point: 302 °C
Enthalpy of Vaporization: 86.23 kJ/mol
Boiling Point: 575.8 °C at 760 mmHg
Vapour Pressure: 2.93E-13 mmHg at 25°C
SMILES: O=S(=O)(c1sc2c(c1)C(NCC)CC(C)S2(=O)=O)N
InChI: InChI=1/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)
InChIKey: IAVUPMFITXYVAF-UHFFFAOYAE
Std. InChI: InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)
Std. InChIKey: IAVUPMFITXYVAF-UHFFFAOYSA-N

Dorzolamide Uses

Dorzolamide (CAS NO.120279-96-1) is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent and topically applied in the form of eye drops.

Product Name

Dorzolamide

Synthetic route

Dorzolamide Chemical Properties

Dorzolamide Uses

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