N-Boc-beta-bromoalanine benzyl ester → (2R)-3-bromo-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

HRID 2217145Notes

Reaction equation

HRID 2217145 reaction equation
C([O:8][C:9](=[O:21])[C@H:10]([CH2:19][Br:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1>O1CCCC1.[Pd]>[C:12]([NH:11][C@H:10]([C:9]([OH:21])=[O:8])[CH2:19][Br:20])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 11772725N-Boc-beta-bromoalanine benzyl ester

Product 1

HCID 20828146(2R)-3-bromo-2-{[(tert-butoxy)carbonyl]amino}propanoic acidYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The N-Boc-β-bromoalanine benzyl ester (22.0 g, 61.41 mmoles) was dissolved in tetrahydrofuran (160-180 mL) and treated with 10% Pd—C (10-15% w/w). The suspension was stirred under hydrogen atmosphere overnight. The mixture was filtered and the solvents removed to afford ˜17.0 g of the Boc-β-bromoalanine free acid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents removed

Sources & evidence

ORD record
ord-45c1abd5cd77411e8a547fbeeb483f56
Source dataset
uspto-grants-2008_08
Patent number
US07407952B2

Reaction notes

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