Trifluoroacetic acid → HCID 86609168, compound

HRID 1161942Notes

Reaction equation

HRID 1161942 reaction equation
C(OC([N:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:12]1[C:18]1[N:19]([CH3:37])[C:20](=[O:36])[C:21]([OH:35])=[C:22]([C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[O:25])[N:23]=1)=O)C1C=CC=CC=1.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>CO.[Pd]>[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[F:17][C:14]1([F:16])[CH2:15][NH2+:11][C@H:12]([C:18]2[N:19]([CH3:37])[C:20](=[O:36])[C:21]([OH:35])=[C:22]([C:24]([NH:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)=[O:25])[N:23]=2)[CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54677624HCID 54677624, compound

Product 1

HCID 86609168HCID 86609168, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl-(2S)-4,4-difluoro-2-(4-{[(4-fluorobenzyl)amino]carbonyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)pyrrolidine-1-carboxylate in MeOH was treated with Pd/C 10% wt (10% w/w) for 3 hours at room temperature under H2 atmosphere. The mixture was filtrated over a celite pad, concentrated in vacuo and treated with trifluoroacetic acid (10 eq.). The acid in excess was removed in vacuo to obtain title product as a pale yellow solid after trituration with ethyl ether.

Workup

  1. filtrationThe mixture was filtrated over a celite pad
  2. concentrationconcentrated in vacuo
  3. customThe acid in excess was removed in vacuo

Sources & evidence

ORD record
ord-71ea828a625a48d4b99ccb1ea83aef3c
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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