tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hex-5-enoate → tert-butyl (3r)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hexanoate

HRID 1700997Notes

Reaction equation

HRID 1700997 reaction equation
[CH3:1][C:2]([CH3:45])([CH3:44])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=2)=[CH:31][CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>[Pd]>[CH3:1][C:2]([CH3:45])([CH3:44])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=2)=[CH:31][CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])[C:4]([OH:6])=[O:5]

Participants

3

Reactant 1

HCID 59875766tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hex-5-enoate

Product 1

HCID 59875740tert-butyl (3r)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-(3'-methoxy-2-methylbiphen-4-yl)hexanoateYield 74,741.703%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to the method of Preparation 19 c), tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-(3′-methoxy-2-methylbiphen-4-yl]hex-5-enoate (1.040 g, 1.69 mmol) was hydrogenated over 10% palladium on charcoal to give tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-(3′-methoxy-2-methylbiphen-4-yl)hexanoate (664 g, 75%) as a colourless foam.

Sources & evidence

ORD record
ord-fdb9bfcf3b4f4afeb180eb2a68130878
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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