(2R, 4E)-N-{(1S)-1-[(benzyloxy)carbonyl]-2,2-dimethylpropyl}-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pent-4-enamide → (2R)-N-[(1S)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamide

HRID 1701013Notes

Reaction equation

HRID 1701013 reaction equation
C([O:8][C:9]([C@@H:11]([NH:16][C:17](=[O:48])[C@@H:18]([C@H:40]1[C:44](=[O:45])[O:43][C:42]([CH3:47])([CH3:46])[O:41]1)[CH2:19]/[CH:20]=[CH:21]/[CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[CH:27][CH:26]=1)[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([C@@H:11]([NH:16][C:17](=[O:48])[C@@H:18]([C@H:40]1[C:44](=[O:45])[O:43][C:42]([CH3:47])([CH3:46])[O:41]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[CH:27][CH:26]=1)[C:12]([CH3:15])([CH3:14])[CH3:13])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 131723129(2R, 4E)-N-{(1S)-1-[(benzyloxy)carbonyl]-2,2-dimethylpropyl}-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pent-4-enamide

Product 1

HCID 131723127(2R)-N-[(1S)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamideYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2R, 4E)-N-{(1S)-1-[(benzyloxy)carbonyl]-2,2-dimethylpropyl}-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pent-4-enamide (534 mg, 0.87 mmol) in ethanol (75 mL) was hydrogenated over 10% palladium on charcoal (50 mg) at 3 bar and 20° C. for 5.75 h. The mixture was filtered through Arbocel filter aid, concentrated under reduced pressure and azeotroped with ethyl acetate to give (2R)-N-[(1s)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pentanamide (384 mg, 61%), as a white solid, which was used for Examples 30 and 31 without purification.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationconcentrated under reduced pressure
  4. customazeotroped with ethyl acetate

Sources & evidence

ORD record
ord-dee798f7f7654395862f8b600d132665
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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