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

HRID 1264572Notes

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

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

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

Sources & evidence

ORD record: ord-0d5d2757a9794632b4541883542b925a
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544984B1

Reaction notes

Loading…