di-tert-butyl (4S)-4-{4-[2-(benzyloxy)ethoxy]-3-tert-butoxybenzyl}-N-(tert-butoxycarbonyl)-L-glutamate → di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[3-tert-butoxy-4-(2-hydroxyethoxy)benzyl]-L-glutamate

HRID 591326Notes

Reaction equation

HRID 591326 reaction equation
C([O:8][CH2:9][CH2:10][O: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][C:13]=1[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])C1C=CC=CC=1>CO.[Pd].[H][H]>[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]([O:11][CH2:10][CH2:9][OH:8])=[C:13]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[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

5

Reactant 1

HCID 117812703di-tert-butyl (4S)-4-{4-[2-(benzyloxy)ethoxy]-3-tert-butoxybenzyl}-N-(tert-butoxycarbonyl)-L-glutamate

Product 1

HCID 117812680di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[3-tert-butoxy-4-(2-hydroxyethoxy)benzyl]-L-glutamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of 340 mg (0.506 mmol) di-tert-butyl (4S)-4-{4-[2-(benzyloxy)ethoxy]-3-tert-butoxybenzyl}-N-(tert-butoxycarbonyl)-L-glutamate in 5 ml methanol was added a little amount of palladium on carbon. The solution is stirred in hydrogen atmosphere for 4 hours. The reaction mixture is filtrated. The filtrate is concentrated. The crude product is concentrated in vacuo. The crude product (310 mg) was used in the following reaction without further purification.

Workup

  1. filtrationThe reaction mixture is filtrated
  2. concentrationThe filtrate is concentrated
  3. concentrationThe crude product is concentrated in vacuo
  4. customThe crude product (310 mg) was used in the following reaction without further purification

Sources & evidence

ORD record
ord-18214bfbeeba42de8b850dcfa0ecdab3
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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