di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{(E)-3-[4-(3-hydroxypropyl)phenyl]prop-2-en-1-yl}-L-glutamate → Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{3-[4-(3-hydroxypropyl)phenyl]propyl}-L-glutamate

HRID 591289Notes

Reaction equation

HRID 591289 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:10][C@H:11]([CH2:19]/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:10][C@H:11]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 89136299di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{(E)-3-[4-(3-hydroxypropyl)phenyl]prop-2-en-1-yl}-L-glutamate

Product 1

HCID 70957113Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{3-[4-(3-hydroxypropyl)phenyl]propyl}-L-glutamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 316 mg (0.59 mmol) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-{(E)-3-[4-(3-hydroxypropyl)phenyl]prop-2-en-1-yl}-L-glutamate in 29 mL of methanol, palladium (10% on charcoal, 126 mg) was added and the suspension was stirred overnight at room temperature under a hydrogen atmosphere. The mixture was filtered over celite, and the solvent was evaporated. The remaining material was used without purification.

Workup

  1. filtrationThe mixture was filtered over celite
  2. customthe solvent was evaporated
  3. customThe remaining material was used without purification

Sources & evidence

ORD record
ord-a59b87b5888545aca007ada5ec615314
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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