HCID 117778092, compound → di-tert-butyl 4-(4-hydroxybenzyl)-L-glutamate

HRID 591332Notes

Reaction equation

HRID 591332 reaction equation
C([O:8][C:9]1[CH:52]=[CH:51][C:12]([CH2:13][CH:14]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:15][C@@H:16]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[NH:17]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:15][C@@H:16]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[NH2:17])=[CH:51][CH:52]=1

Participants

4

Reactant 1

HCID 117778092HCID 117778092, compound

Product 1

HCID 70977414di-tert-butyl 4-(4-hydroxybenzyl)-L-glutamateYield 28.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Di-tert-butyl 4-[4-(benzyloxy)benzyl]-N-trityl-L-glutamate (499 mg, 0.72 mmol) were dissolved in methanol (20 ml). Palladium (10% on charcoal) (228 mg; 214 μmol) was added and the suspension was shaken under a hydrogen atmosphere for 12 h. The reaction mixture was filtered through a pad of celite, concentrated under reduced pressure and the residue was purified by silica gel column chromatography to yield 75 mg (28.7%) of the product.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1963823dbda4c8e8db32c4ca6461ee5
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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