3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide

Base Information

Chemical Name:3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide
CAS No.:222631-52-9
Molecular Formula:C₁₀H₁₆N₄O₄
Molecular Weight:256.261
Hs Code.:
DSSTox Substance ID:DTXSID20698483
Mol file:222631-52-9.mol

Synonyms:222631-52-9;DTXSID20698483;3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide;1H-Pyrrole-2-carboxamide, 3-amino-4-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl]-

Suppliers and Price of 3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide

Chemical Property:

PSA：158.61000
LogP:-0.78300
XLogP3:-2.3
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:256.11715500
Heavy Atom Count:18
Complexity:329

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=C(C(=C(N1)C(=O)N)N)C2C(C(C(N2)CO)O)O

Technology Process of 3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide

There total 9 articles about 3-Amino-4-[3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrrole-2-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 4-(4-amino-1-benzyloxycarbonyl-5-carbamoyl-1H-pyrrol-3-yl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

: 222631-52-9
(1S)-1-(3-amino-2-carboxamidopyrrol-4-yl)-1,4-dideoxy-1,4-imino-D-ribitol

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 16h;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

: 153172-31-7
(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 222631-52-9
(1S)-1-(3-amino-2-carboxamidopyrrol-4-yl)-1,4-dideoxy-1,4-imino-D-ribitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: NCS / pentane / 1 h

1.2: LiTMP / tetrahydrofuran / -78 °C

2.1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

3.1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylformamide / 1 h / 65 - 70 °C

5.1: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

6.1: NaOAc / methanol / 16 h / 20 °C

7.1: DBU / CH₂Cl₂ / 4 h / Heating

8.1: aq. H₂O₂; K₂CO₃ / dimethylsulfoxide / 0.17 h

9.1: 10 mg / aq. TFA / 16 h / 20 °C

With N-chloro-succinimide; dihydrogen peroxide; sodium acetate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 1.1: Chlorination / 1.2: Elimination / 2.1: Addition / 3.1: Substitution / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Condensation / 7.1: Substitution / 8.1: Addition / 9.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

: 153172-33-9
(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 222631-52-9
(1S)-1-(3-amino-2-carboxamidopyrrol-4-yl)-1,4-dideoxy-1,4-imino-D-ribitol

Guidance literature:: Multi-step reaction with 8 steps

1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

2: 85 percent / CH₂Cl₂ / 16 h / 20 °C

3: dimethylformamide / 1 h / 65 - 70 °C

4: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

5: NaOAc / methanol / 16 h / 20 °C

6: DBU / CH₂Cl₂ / 4 h / Heating

7: aq. H₂O₂; K₂CO₃ / dimethylsulfoxide / 0.17 h

8: 10 mg / aq. TFA / 16 h / 20 °C

With dihydrogen peroxide; sodium acetate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Addition / 2: Substitution / 3: Condensation / 4: Hydrolysis / 5: Condensation / 6: Substitution / 7: Addition / 8: Hydrolysis;
DOI:10.1016/S0040-4020(00)00194-0