Ammonium formate → (S)-tert-Butyl 2-amino-3-hydroxypropanoate

HRID 1420580Notes

Reaction equation

HRID 1420580 reaction equation
C(OC([NH:11][C@H:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][O:14]CC1C=CC=CC=1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:11][C@H:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][OH:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15778647N-(Benzyloxycarbonyl)-O-benzylserine, t-butyl ester2×

Product 1

HCID 11768865(S)-tert-Butyl 2-amino-3-hydroxypropanoateYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 29.24 g (0.076 mol) of (L) N-(benzyloxycarbonyl)-O-benzylserine, t-butyl ester from Reference Example 1, 24.1 g (0.38 mol) of ammonium formate and 38.3 g of 10% palladium on carbon in 600 ml of methanol was heated at 65° C. for 20 hours and stirred at room temperature overnight. The mixture was filtered through diatomaceous earth and the filter pad was washed with methanol. The filtrate was concentrated to give 12.18 g (99.6%) of product as described in Synthetic Commun., 26:2723 (1996).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a4502778dbda4127844521c2d8de52b5
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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