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

HRID 1433796Notes

Reaction equation

HRID 1433796 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 (1.86 g, 3.57 mmol) in methanol (50 mL) was purged with nitrogen and 10% palladium on carbon (100 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 of sufficient purity for subsequent use without additional purification (0.88 g, 73%).

Workup

  1. customwas purged with nitrogen and 10% palladium on carbon (100 mg)
  2. additionadded
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-106306080eff46dea8e846496f273e1b
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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