Di-tert-butyl (4S)-4-{4-[3-(benzyloxy)propyl]benzyl}-N-(tert-butoxycarbonyl)-L-glutamate → Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[4-(3-hydroxypropyl)benzyl]-L-glutamate

HRID 591267Notes

Reaction equation

HRID 591267 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:43]=[CH:42][C:15]([CH2:16][C@H:17]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:18][C@@H:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:14][CH:13]=1)C1C=CC=CC=1>CO.[Pd]>[C:24]([O:23][C:21]([NH:20][C@H:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:18][C@H:17]([CH2:16][C:15]1[CH:42]=[CH:43][C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=1)[C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 131734509Di-tert-butyl (4S)-4-{4-[3-(benzyloxy)propyl]benzyl}-N-(tert-butoxycarbonyl)-L-glutamate

Product 1

HCID 70957093Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[4-(3-hydroxypropyl)benzyl]-L-glutamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

To a solution of 690 mg (1.15 mmol) di-tert-butyl (4S)-4-{4-[3-(benzyloxy)propyl]benzyl}-N-(tert-butoxycarbonyl)-L-glutamate in 17 mL of methanol, palladium (10% on charcoal) 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-18cb67082fdf47aba5c32b399b2581a9
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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