(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate → HCID 178502274, compound

HRID 388906Notes

Reaction equation

HRID 388906 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][C@H:14]([NH:25][C:26]([O:28][CH3:29])=[O:27])[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[N:10]=[N:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:29][O:28][C:26]([NH:25][C@@H:14]([CH2:13][C:11]1[N:10]=[N:9][NH:8][CH:12]=1)[C:15]([OH:17])=[O:16])=[O:27]

Participants

4

Reactant 1

HCID 71182684(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate

Product 1

HCID 178502274HCID 178502274, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-Benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate (502 mg, 1.11 mmol) was hydrogenated in the presence of Pd—C (82 mg) in MeOH (5 mL) at atmospheric pressure for 12 h. The mixture was filtered through diatomaceous earth (CELITE®) and concentrated in vacuo. (S)-2-(methoxycarbonylamino)-3-(1H-1,2,3-triazol-4-yl)propanoic acid was obtained as a colorless gum (266 mg, 111%) which was contaminated with ca. 10% of the methyl ester. The material was used as is without further purification. 1H NMR (400 MHz, DMSO-d6) δ 12.78 (s, br, 1H), 7.59 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 4.19-4.24 (m, 1H), 3.49 (s, 3H), 3.12 (dd, J=4.8 Hz, 14.9 Hz, 1H), 2.96 (dd, J=9.9, 15.0 Hz, 1H). LC-MS: Anal. Calcd. for C7H10N4O4: 214. found: 215 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth (CELITE®)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e06f236f50b243fdae2f19106d31406c
Source dataset
uspto-grants-2013_02
Patent number
US08377980B2

Reaction notes

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