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inquiry[English Name] Dorzolamide [CAS No.] 120279-96-1 [Mol. Formula ] C10H16N2O4S3 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:drum Application:Eye Treatment Drug; Miotic, Antiglaucoma Transportation:B
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(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide
dorzolamide
Conditions | Yield |
---|---|
With zinc(II) tetrahydroborate In methanol at 90℃; for 3h; Temperature; Solvent; Green chemistry; | 90% |
dorzolamide
Conditions | Yield |
---|---|
With hydrogenchloride; water In methanol for 72h; Heating / reflux; | 66% |
dorzolamide
Conditions | Yield |
---|---|
With dimethylsulfide borane complex; sulfuric acid 1) THF, r.t.; Yield given. Multistep reaction; |
(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one
dorzolamide
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 |
5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran
dorzolamide
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 |
(S)-3-(thien-2-ylthio)butyric acid
dorzolamide
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 |
(S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide
dorzolamide
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 |
methyl (S)-3-(thiophen-2-ylthio)butyrate
dorzolamide
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 |
5,6-dihydro-(R,S)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide
dorzolamide
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 |
dorzolamide
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 |
dorzolamide
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 |
dorzolamide
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 |
dorzolamide
dorzolamide hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethyl acetate pH=1; | 95% |
With hydrogenchloride In water; dimethyl sulfoxide at 5 - 10℃; for 3h; pH=1.0; |
docosahexaenoic acid
dorzolamide
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% |
N,N-dimethyl-formamide dimethyl acetal
dorzolamide
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
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 | 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
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 | 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% |
BOC-glycine
dorzolamide
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% |
dorzolamide
tert-butylchlorodiphenylsilane
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% |
dorzolamide
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% |
dorzolamide
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% |
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 | 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% |
dorzolamide
(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid
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% |
dorzolamide
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% |
dorzolamide
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% |
dorzolamide
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 1h; | 65% |
dorzolamide
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% |
dorzolamide
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% |
dorzolamide
Acetoxyacetyl chloride
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% |
carbonochloridic acid, chloromethyl ester
dorzolamide
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; |
dorzolamide
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% |
dorzolamide
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% |
dorzolamide
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% |
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 | 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% |
dorzolamide
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% |
acetic anhydride
dorzolamide
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% |
dorzolamide
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% |
dorzolamide
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% |
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 | 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% |
dorzolamide
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% |
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