HCID 57433087, compound → HCID 57433088, compound

HRID 1675180Notes

Reaction equation

HRID 1675180 reaction equation
[N:1]([C@@H:4]([C@@H:13]([OH:30])[C@@H:14]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([NH:7][CH:8]([CH3:12])[CH2:9][CH2:10][CH3:11])=[O:6])=[N+]=[N-]>CO>[NH2:1][C@@H:4]([C@@H:13]([OH:30])[C@@H:14]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([NH:7][CH:8]([CH3:12])[CH2:9][CH2:10][CH3:11])=[O:6]

Participants

3

Reactant 1

HCID 57433087HCID 57433087, compound

Product 1

HCID 57433088HCID 57433088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,3S,4S)-2-azido-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-N-(1-methylbutyl)-5-phenylpentanamide (55 mg, 0.131 mmol) in MeOH (4 mL) which had been degassed and purged with nitrogen was added a small amount of 10% Pd on carbon. The mixture was flushed again with nitrogen and stirred overnight under a balloon atmosphere of hydrogen. The reaction was filtered and the resulting filtrate concentrated in vacuo to afford the product as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.25-7.23 (m, 4H), 7.17-7.15 (m, 1H), 3.91-3.86 (m, 2H), 3.66-3.59 (m, 1H), 3.32-3.30 (m, 1H), 3.21-3.17 (m, 1H), 2.59-2.52 (m, 1H), 1.52-1.33 (m, 4H), 1.29 (s, 9H), 1.26-1.12 (m, 3H), 0.95-0.91 (m, 3H); ES MS (M+1)=394.

Workup

  1. custompurged with nitrogen
  2. additionwas added a small amount of 10% Pd on carbon
  3. customThe mixture was flushed again with nitrogen
  4. filtrationThe reaction was filtered
  5. concentrationthe resulting filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e538bb84c62141a39df3a36aef5408c8
Source dataset
uspto-grants-2011_08
Patent number
US08003653B2

Reaction notes

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