HCID 86634555, compound → HCID 15940236, compound

HRID 1014159Notes

Reaction equation

HRID 1014159 reaction equation
[CH:1]1([CH2:6][CH:7]([CH2:27][N:28]([CH:37]=[O:38])[O:29]CC2C=CC=CC=2)[C:8]([N:10]2[CH2:26][CH2:25][CH2:24][C@H:11]2[C:12]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])=[O:13])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([CH2:6][C@H:7]([CH2:27][N:28]([CH:37]=[O:38])[OH:29])[C:8]([N:10]2[CH2:26][CH2:25][CH2:24][C@H:11]2[C:12]([NH:14][C:15]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[O:16])=[O:13])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86634555HCID 86634555, compound

Product 1

HCID 15940236HCID 15940236, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-[(4-fluorophenyl)carbonyl]-L-prolinamide (0.34 mmol, 180 mg) was dissolved in MeOH (3 mL) and the solution was degassed. 10% Pd/C or Pd/BaSO4 (36 mg) was added and the suspension was charged with H2 via balloon. The reaction was stirred under H2 atmosphere for 1 hour, then filtered and concentrated to provide 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-[(4-fluorophenyl)carbonyl]-L-prolinamide (Example 1) in quantitative yield.

Workup

  1. customthe solution was degassed
  2. addition10% Pd/C or Pd/BaSO4 (36 mg) was added
  3. additionthe suspension was charged with H2 via balloon
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82f3e2c24fb24b1fba2f12e7058bdd59
Source dataset
uspto-grants-2011_07
Patent number
US07982053B2

Reaction notes

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