benzyl (2S,3S)-3-hydroxy-2-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)hex-4-ynylcarbamate → HCID 67272196, compound

HRID 250807Notes

Reaction equation

HRID 250807 reaction equation
[OH:1][C@@H:2]([C:35]#[C:36][CH3:37])[C@@H:3]([N:16]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:17]1=[O:34])[CH2:4][NH:5]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:5][CH2:4][C@H:3]([N:16]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:32])[F:30])[CH:24]=2)[C:17]1=[O:34])[C@@H:2]([OH:1])[CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 1

HCID 86614496benzyl (2S,3S)-3-hydroxy-2-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)hex-4-ynylcarbamate

Product 1

HCID 67272196HCID 67272196, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (2S,3S)-3-hydroxy-2-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)hex-4-ynylcarbamate (0.32 g) in MeOH (5 mL) was charged with 10% Pd/C and then stirred under H2 (1 atm) for 5 h at RT, filtered through diatomaceous earth, and concentrated in vacuo to provide N-((S)-1-((2S,3S)-1-amino-3-hydroxyhexan-2-yl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide (0.24 g). MS found: (M+H)+=388.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5de16752b544244baa8e6ed6b367da4
Source dataset
uspto-grants-2011_01
Patent number
US07863317B2

Reaction notes

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