(R)-[4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid → HCID 67001303, compound

HRID 561991Notes

Reaction equation

HRID 561991 reaction equation
C([O:8][CH2:9][CH:10]([CH2:30][O:31]CC1C=CC=CC=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1)C1C=CC=CC=1>CO>[C:26]([O:25][C:23]([NH:22][C@H:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH:10]([CH2:9][OH:8])[CH2:30][OH:31])=[CH:13][CH:14]=1)[C:19]([OH:21])=[O:20])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 1

HCID 67001437(R)-[4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid

Product 1

HCID 67001303HCID 67001303, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A hydrogenation vessel containing a solution of (R)-[4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid (3.86 g, 7.4 mmol) in methanol (30 mL) was purged with nitrogen and 10% palladium on carbon (300 mg) added. The atmosphere above the methanol solution was exchanged for hydrogen and the reaction mixture stirred vigorously for 30 minutes at ambient temperature. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to give (R)-tert-butoxycarbonylamino-[4-(2-hydroxy-1-hydroxymethyl-ethoxy)-phenyl]-acetic acid which was used without additional purification (2.43 g, 96%). HR-MS: calcd for C30H28FlN4O5 [M+H+] 671.1161. Found 671.1158.

Workup

  1. customwas purged with nitrogen and 10% palladium on carbon (300 mg)
  2. additionadded
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-923cc0fcb87d4b55ba21381faad02c6f
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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