(S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate → (S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoic acid

HRID 630633Notes

Reaction equation

HRID 630633 reaction equation
[CH3:1][CH:2]([CH3:45])[CH2:3][C@H:4]([N:15]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:16](=[O:36])[C@@H:17]([NH:26][C:27](=[O:35])[CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6]>CO.O.CO.[Pd]>[CH3:1][CH:2]([CH3:45])[CH2:3][C@H:4]([N:15]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:16](=[O:36])[C@@H:17]([NH:26][C:27](=[O:35])[CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 1

HCID 86715394(S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate

Product 1

HCID 86715393(S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoic acidYield 92.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Referring to FIG. 45, a slurry of Pd/C (10%) (200 mg) in MeOH/water (9:1) (10 mL) was added to a solution of (S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate (440 mg, 0.7 mmol) in MeOH (100 mL) and the suspension was stirred overnight under an atmosphere of hydrogen at RT. The reaction mixture was filtered over Celite, washed with MeOH and concentrated in vacuo to yield product (345 mg, 92%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fac1aff7a604d078446edb4f6adc527
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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