1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide → 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamide

HRID 1014158Notes

Reaction equation

HRID 1014158 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:18][N:19]([CH:28]=[O:29])[O:20]CC2C=CC=CC=2)[C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([NH2:14])=[O:13])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([CH2:6][C@H:7]([CH2:18][N:19]([CH:28]=[O:29])[OH:20])[C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([NH2:14])=[O:13])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 578781271-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide

Product 1

HCID 578781071-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamideYield 113%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide (24 g, 0.060 mol) was dissolved in MeOH (500 mL) and degassed. Catalyst (10% Pd/C, Degussa type, wet, 2.4 g) was added and the mixture was stirred under a hydrogen balloon for 3 hours. After degassing, the suspension was filtered through Celite, washing with methanol, and the filtrate was concentrated. The resulting foam was dissolved in ethyl acetate (50 mL) and diluted with toluene (˜500 mL.) This solution was then concentrated to a slurry (˜100 mL) and diluted with hexanes (200 mL.) Filtration, washing with hexanes and drying afforded the product 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamide (21 g, 113% yield). The excess yield is due to residual toluene. LC/MS m/z 312 (MH+)

Workup

  1. customdegassed
  2. additionCatalyst (10% Pd/C, Degussa type, wet, 2.4 g) was added
  3. customAfter degassing
  4. filtrationthe suspension was filtered through Celite
  5. washwashing with methanol
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe resulting foam was dissolved in ethyl acetate (50 mL)
  8. additiondiluted with toluene (˜500 mL.) This solution
  9. concentrationwas then concentrated to a slurry (˜100 mL)
  10. additiondiluted with hexanes (200 mL.) Filtration
  11. washwashing with hexanes
  12. customdrying

Sources & evidence

ORD record
ord-9b0768a6c008485db2111e43a2c3e9f4
Source dataset
uspto-grants-2011_07
Patent number
US07982053B2

Reaction notes

Loading…