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Methanol → (3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

HRID 363868
Notes
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Reaction equation

HRID 363868 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@@H:30](CNC1C=CC=CC=1[N+]([O-])=O)[C:31]([OH:33])=[O:32])=O)(C)(C)C.[CH3:45]O>[Pd]>[CH3:45][O:33][C:31](=[O:32])[CH2:30][N:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]1=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 22881946(S)-3-((2-Aminophenyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acidHCID 22881947N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine

Product 1

HCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938
Palladium
Catalyst

Procedure

(2S)-2-tert-Butoxycarbonylamino-3-(2-aminophenyl-amino)-propionic acid. A mixture of (2S)-2-tert-Butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (12.65 g, 40.5 mmol) and 0.5 g of 10% Pd/C in 100 ml of MeOH under hydrogen at 1 atmosphere was stirred for 4 h. The solution was filtered through Celite 545 and the filtrate evaporated in vacuo to afford the 11.95 g of the title compound in quantitative yield as a dark brown solid that was used without purification: 1H NMR (CD3OD) δ 6.75-6.70 (3H,m), 6.65-6.58 (1H, m), 4.35-4.3 1H, m), 3.6-3.38 (2H, m), 1.45 (9H, s).

Workup

  1. filtrationThe solution was filtered through Celite 545
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-8f7b71dec6cf4da692f841638efa922a
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05874424

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes