Ethyl Acetate → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pentanamide

HRID 1700988Notes

Reaction equation

HRID 1700988 reaction equation
[CH3:1][C:2]1([CH3:45])[O:6][C@@H:5]([C@@H:7]([CH2:27]/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:32]([F:43])[CH:31]=2)[C:8]([NH:10][C@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:9])[C:4](=[O:44])[O:3]1.C(OCC)(=O)C>C(O)C.[Pd]>[CH3:45][C:2]1([CH3:1])[O:6][C@@H:5]([C@@H:7]([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:32]([F:43])[CH:31]=2)[C:8]([NH:10][C@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])=[O:17])[C:12]([CH3:13])([CH3:14])[CH3:15])=[O:9])[C:4](=[O:44])[O:3]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59875800(2R, 5E)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pent-4-enamide

Product 1

HCID 57123432(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pentanamideYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2R, 5E)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pent-4-enamide (210 mg, 0.34 mmol) in ethanol:ethyl acetate=5:1 (10 mL) was hydrogenated over 10% palladium on charcoal (20 mg) at 3 bar and 20° C. for 3 h. The mixture was filtered through Arbocel filter aid and concentrated under reduced pressure to give (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pentanamide (103 mg, 49%), as a colourless solid, which was used for Example 9 without purification.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8d02bf059d645e99d53d2368177ca2e
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

Loading…