Acetic Anhydride → HCID 178499096, compound

HRID 1161924Notes

Reaction equation

HRID 1161924 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C@@H:22]2[CH2:26][C@H:25]([F:27])[CH2:24][N:23]2[C:28]([O:30]CC2C=CC=CC=2)=O)[N:8](C)[C:9](=[O:20])[C:10]=1[O:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[C:38](OC(=O)C)(=O)C>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([OH:20])[N:8]=[C:7]([C@@H:22]2[CH2:26][C@H:25]([F:27])[CH2:24][N:23]2[C:28](=[O:30])[CH3:38])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 23626787HCID 23626787, compound

Product 1

HCID 178499096HCID 178499096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl-5-(benzoyloxy)-2-{(2S,4S)-1-[(benzyloxy)carbonyl]-4-fluoropyrrolidin-2-yl}-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate, dissolved in ethyl acetate was treated with Pd/C 10% (10% w/w) and acetic anhydride (1 eq.) and submitted under H2 atmosphere at room temperature. The reaction mixture was stirred at room temperature for 18 hours and then the suspension was filtered over celite to give the title compound as a 7:3 mixture of rotamers by NMR.

Workup

  1. customsubmitted under H2 atmosphere at room temperature
  2. filtrationthe suspension was filtered over celite

Sources & evidence

ORD record
ord-53e4edec264d4347a56dbeb53dbf9474
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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