(2R)-2-azido-N-benzyl-3-hydroxypropanamide → (2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

HRID 1852050Notes

Reaction equation

[N:1]([C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

Conditions

Temperature: 27.5 °C

Procedure

In an autoclave charged (2R)-2-azido-N-benzyl-3-hydroxypropanamide (68.0 gms) in ethyl acetate (680 ml). Charged catalyst 5% Pd-C (6.85 gms) and closed the autoclave. Applied 3.8 kg Hydrogen pressure maintaining temperature at 25-30° C. and maintained the reaction mixture at 25-30° C. for 1.0 hour. After completion of the reaction, released Hydrogen pressure and flushed the autoclave with Nitrogen gas. Filtered the reaction mass through hyflo bed and washed hyflo bed with ethyl acetate. Concentrated filtrate under reduced pressure at 30-35° C. till two volumes of ethyl acetate remains in the reaction mixture. Removed vacuum and cooled the reaction mass to 0-5° C. and maintained for 2.0 hours. The reaction mass was filtered and washed with cold ethyl acetate (2×40 ml). Dried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight.

Workup

customAfter completion of the reaction
customflushed the autoclave with Nitrogen gas
filtrationFiltered the reaction mass through hyflo bed
washwashed
customat 30-35° C.
customRemoved vacuum
temperaturecooled the reaction mass to 0-5° C.
temperaturemaintained for 2.0 hours
filtrationThe reaction mass was filtered
washwashed with cold ethyl acetate (2×40 ml)
dry with materialDried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight

Sources & evidence

ORD record: ord-086fcebc55394129afee68dbab3c5fc5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957252B2

Reaction notes

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