N10-(Trifluoroacetyl)pteroic acid supplier

Name
N10-(TRIFLUOROACETYL)PTEROIC ACID
EINECS
CAS No. 37793-53-6
Article Data16
CAS DataBase
Density 1.74g/cm³
Solubility
Melting Point 270 °C (dec.)(lit.)
Formula C16H11 F3 N6 O4
Boiling Point 650.2°Cat760mmHg
Molecular Weight 408.296
Flash Point 347.1°C
Transport Information
Appearance
Safety Hazard Codes T
Risk Statements 45-20/21/22-36/37/38
Safety Statements 53-22-26-36/37/39-45
WGK Germany 3
Risk Codes 45-20/21/22-36/37/38
Molecular Structure
Hazard Symbols
Synonyms Benzoicacid, 4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl](trifluoroacetyl)amino]-(9CI);N10-(Trifluoroacetyl)pteroic acid;N10-Trifluoroacetylpteroic acid;
PSA 155.42000
LogP 2.08250

Synthetic route

: 223378-68-5
N10-(trifluoroacetyl)pyrofolic acid

A: 37793-53-6
N10-trifluoroacetylpteroic acid

B: 2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-pentanedioic acid

Conditions

Conditions	Yield
With hydrogenchloride Hydrolysis;	A 56% B 33%

: 59-30-3
folic acid

: 37793-53-6
N10-trifluoroacetylpteroic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 10.5 h / 0 - 25 °C 1.2: 123 g / ice / tetrahydrofuran / 3 h / 25 °C 2.1: 56 percent / aq. HCl View Scheme

: 197151-79-4
pteroyl azide

: 37793-53-6
N10-trifluoroacetylpteroic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 67 percent / tetramethylguanidine / dimethylsulfoxide / 9 h / 25 °C 2.1: tetrahydrofuran / 10.5 h / 0 - 25 °C 2.2: 123 g / ice / tetrahydrofuran / 3 h / 25 °C 3.1: 56 percent / aq. HCl View Scheme

: 119-24-4
pteroic acid

: 407-25-0
trifluoroacetic anhydride

: 37793-53-6
N10-trifluoroacetylpteroic acid

Conditions

Conditions	Yield
Stage #1: pteroic acid; trifluoroacetic anhydride at 20℃; for 96h; Stage #2: With trifluoroacetic acid In water for 48.3333h;
at 20℃; for 24h; Inert atmosphere; Darkness;
With trifluoroacetic acid
at 20℃; for 24h; Inert atmosphere; Darkness;

: 119-24-4
pteroic acid

: 76-05-1
trifluoroacetic acid

: 407-25-0
trifluoroacetic anhydride

: 37793-53-6
N10-trifluoroacetylpteroic acid

Conditions

Conditions	Yield
Stage #1: pteroic acid; trifluoroacetic anhydride at 20℃; for 96h; Sealed tube; Inert atmosphere; Stage #2: trifluoroacetic acid at 20℃; for 48h; Sealed tube; Inert atmosphere;

...Expand

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 2-aminopentanedicarboxylic acid 5-tert-butyl ester 1-methyl ester

: C26H28F3N7O7

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	100%

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 6234-01-1
L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride

: (S)-5-tert-butyl 1-methyl 2-(4-{N-[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]-2,2,2-trifluoroacetamido}benzamido)pentanedioate

Conditions

Conditions	Yield
Stage #1: N10-trifluoroacetylpteroic acid; L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 23℃; for 0.25h; Inert atmosphere; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 23℃; for 24h; Inert atmosphere;	100%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 23℃; Inert atmosphere;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: C17H33N3O7

: (S)-methyl 18-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-2,2-dimethyl-4,15-dioxo-3,8,11-trioxa-5,14-diazanonadecan-19-oate

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Inert atmosphere;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Inert atmosphere;	4.06 g
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Inert atmosphere;	4.06 g

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 17083-23-7
2-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester

: C33H36F3N7O6

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 23℃; for 2.16667h; Inert atmosphere;	96.7%

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 1375540-44-5
(S)-tert-butyl 2-amino-5-((3-azidopropyl)amino)-5-oxopentanoate

: 1375540-45-6
(S)-tert-butyl 2-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-5-((3-azidopropyl)amino)-5-oxopentanoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 48h;	52%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 2,5-dioxopyrrolidin-1-yl 4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide at 20℃; for 14h;	51%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 20℃; for 24h;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: C39H57N3O11

: C40H56F3N9O12

Conditions

Conditions	Yield
Stage #1: C39H57N3O11 With diethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N10-trifluoroacetylpteroic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	50%

: 37793-53-6
N10-trifluoroacetylpteroic acid

: C39H57N3O11

: C40H56F3N9O12

Conditions

Conditions	Yield
Stage #1: C39H57N3O11 With diethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N10-trifluoroacetylpteroic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	50%

: α,γ-bis(L-glutamoyl)-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

: 37793-53-6
N10-trifluoroacetylpteroic acid

: α,γ-bis(L-glutamoyl)-N-[N10-(trifluoroacetyl)pteroyl]-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

Conditions

Conditions	Yield
Stage #1: N10-trifluoroacetylpteroic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: α,γ-bis(L-glutamoyl)-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 72h;	47%

: α,γ-bis(D-glutamoyl)-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

: 37793-53-6
N10-trifluoroacetylpteroic acid

: α,γ-bis(D-glutamoyl)-N-[N10-(trifluoroacetyl)pteroyl]-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

Conditions

Conditions	Yield
Stage #1: N10-trifluoroacetylpteroic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: α,γ-bis(D-glutamoyl)-D-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 72h;	42%

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 13031-60-2
methyl γ-aminobutyrate hydrochloride

: C21H20F3N7O5

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	40%

: α,γ-bis(L-glutamoyl)-L-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

: 37793-53-6
N10-trifluoroacetylpteroic acid

: α,γ-bis(L-glutamoyl)-N-[N10-(trifluoroacetyl)pteroyl]-L-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester

Conditions

Conditions	Yield
Stage #1: N10-trifluoroacetylpteroic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: α,γ-bis(L-glutamoyl)-L-glutamic acid tetra{2-[3,4-di(hexyloxy)phenyl]ethyl} ester In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 72h;	39%

: 37793-53-6
N10-trifluoroacetylpteroic acid

: C21H23N2O3Pol

: 71989-18-9
Fmoc-Glu(OtBu)-OH

: Lys-Glu-N10-(trifluoroacetyl)pteroic acid

Conditions

Conditions	Yield
Stage #1: C21H23N2O3Pol With piperidine In N,N-dimethyl-formamide for 0.166667h; not specified; Stage #2: Fmoc-Glu(OtBu)-OH With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #3: N10-trifluoroacetylpteroic acid With chlorotriisopropylsilane; trifluoroacetic acid In water for 0.5h; Inert atmosphere;	39%

Yield

Stage #1: C21H23N2O3Pol With piperidine In N,N-dimethyl-formamide for 0.166667h; not specified;
Stage #2: Fmoc-Glu(OtBu)-OH With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere;
Stage #3: N10-trifluoroacetylpteroic acid With chlorotriisopropylsilane; trifluoroacetic acid In water for 0.5h; Inert atmosphere;

39%

...Expand

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139974-52-0
methyl DL-2-amino-4-(methylsulfonyl)butanoate hydrochloride

: 115510-52-6
2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-methanesulfonyl-butyric acid

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1.) DMSO, RT, 45 min, 2.) 30-35 deg C, 24 h; Yield given. Multistep reaction;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139895-37-7
methyl DL-2-amino-4-butanoate dihydrochloride

: 115453-76-4
pteroyl-S-methylhomocysteine sulfoximine

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1.) DMSO, RT, 45 min, 2.) 30-35 deg C, 24 h; Yield given. Multistep reaction;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139895-38-8
methyl DL-2-amino-4-butanoate dihydrochloride

: 115453-77-5
pteroyl-S-ethylhomocysteine sulfoximine

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1.) DMSO, RT, 45 min, 2.) 30-35 deg C, 24 h; Yield given. Multistep reaction;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139895-39-9
methyl DL-2-amino-4-butanoate dihydrochloride

: 115453-78-6
pteroyl-S-propylhomocysteine sulfoximine

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1.) DMSO, RT, 45 min, 2.) 30-35 deg C, 24 h; Yield given. Multistep reaction;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139895-40-2
methyl DL-2-amino-4-butanoate dihydrochloride

: 115453-79-7
pteroyl-S-1-butylhomocysteine sulfoximine

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1.) DMSO, RT, 45 min, 2.) 30-35 deg C, 24 h; Yield given. Multistep reaction;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 173315-21-4
(2S,4S)-4-fluoroglutamic acid α,γ-di-tert-butyl ester

: 1025903-77-8
(2S,4S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-4-fluoro-pentanedioic acid di-tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 68h; Ambient temperature;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 139112-62-2
DL-3,3-difluoroglutamic acid α,γ-di-tert-butyl ester

: 2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-3,3-difluoro-pentanedioic acid di-tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide for 72h; Ambient temperature;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 543-27-1
isobutyl chloroformate

: 115255-07-7
C21H19F3N6O6

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
With triethylamine In N,N-dimethyl-formamide at 0℃; for 1h;
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.75h; Inert atmosphere;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 543-27-1
isobutyl chloroformate

: 4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoic acid isobutyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Esterification;

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 84793-07-7
Fmoc-Glu-OtBu

: 71989-14-5
Fmoc-(tBu)Asp-OH

: Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

H2N-Ser(p-methoxytrityl)-O-Wang resin: H2N-Ser(p-methoxytrityl)-O-Wang resin

: C42H50F3N15O18S

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)-amino)-3-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl)amino)propanoic acid

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 84793-07-7
Fmoc-Glu-OtBu

: 71989-14-5
Fmoc-(tBu)Asp-OH

S-Fm-3-thiopropionic acid: S-Fm-3-thiopropionic acid

H-Cys(4-methoxytrityl)-2-chlorotrityl resin: H-Cys(4-methoxytrityl)-2-chlorotrityl resin

: 926623-18-9
C54H59N13O18S2

Conditions

Conditions	Yield
Multistep reaction.;	450 mg

...Expand

: 37793-53-6
N10-trifluoroacetylpteroic acid

: bis{2-[3,4-bis(hexyloxy)phenyl]ethyl} N-[N10-(trifluoroacetyl)pteroyl]-L-glutamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide / 1 h / 20 °C 2: dimethylformamide; tetrahydrofuran / 72 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide / 1 h / 20 °C 2: dimethylformamide; tetrahydrofuran / 40 °C View Scheme

: 37793-53-6
N10-trifluoroacetylpteroic acid

: (5-nitro-2-furyl)methyl Nε-(pteroyllysyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 1 h / 0 °C 2: dimethylformamide / 2 h / 0 °C 3: aq. K2CO3 / methanol; tetrahydrofuran / 144 h / 20 °C View Scheme

: 37793-53-6
N10-trifluoroacetylpteroic acid

: (5-nitro-2-furyl)methyl Nε-(pteroyllysyl)-N,N-bis(2-bromoethyl)phosphorodiamidate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 1 h / 0 °C 2: dimethylformamide / 2 h / 0 °C 3: 89 percent / aq. K2CO3 / methanol; tetrahydrofuran / 144 h / 20 °C View Scheme

: 37793-53-6
N10-trifluoroacetylpteroic acid

: 324770-56-1
(5-nitro-2-furyl)methyl Nε-(N10-(trifluoroacetyl)pteroyllysyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide / 1 h / 0 °C 2: dimethylformamide / 2 h / 0 °C View Scheme

N10-(Trifluoroacetyl)pteroic acid Specification

The N10-(Trifluoroacetyl)pteroic acid, with the CAS registry number 37793-53-6, is also known 4-[(2-Amino-4-hydroxypteridin-6-ylmethyl)-(2,2,2-trifluoroacetyl)amino]benzoic acid.It belongs to the product Organic matters.This chemical's molecular formula is C₁₆H₁₁F₃N₆O₄and molecular weight is 408.2. What's more,Its systematic name is 4-{[(2-Amino-4-oxo-1,4-dihydro-6-pteridinyl)methyl](trifluoroacetyl)amino}benzoic acid.

Physical properties about N10-(Trifluoroacetyl)pteroic acid are: (1)ACD/LogP: 0.44; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.04; (4)ACD/LogD (pH 7.4): -2.51; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.36; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 10; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.698; (13)Molar Refractivity: 90.276 cm3; (14)Molar Volume: 234.096 cm3; (15)Surface Tension: 65.5690002441406 dyne/cm; (16)Density: 1.744 g/cm3; (17)Flash Point: 347.051 °C; (18)Enthalpy of Vaporization: 100.711 kJ/mol; (19)Boiling Point: 650.237 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:FC(F)(F)C(=O)N(c1ccc(C(=O)O)cc1)Cc2nc3c(nc2)N/C(=N\C3=O)N;
(2)Std. InChI:InChI=1S/C16H11F3N6O4/c17-16(18,19)14(29)25(9-3-1-7(2-4-9)13(27)28)6-8-5-21-11-10(22-8)12(26)24-15(20)23-11/h1-5H,6H2,(H,27,28)(H3,20,21,23,24,26);
(3)Std. InChIKey:IJGIHDXKYQLIMA-UHFFFAOYSA-N;

Product Name

N10-(TRIFLUOROACETYL)PTEROIC ACID

Synthetic route

N10-(Trifluoroacetyl)pteroic acid Specification

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Hazard Codes	T
Risk Statements	45-20/21/22-36/37/38
Safety Statements	53-22-26-36/37/39-45
WGK Germany	3