Hydrochloric Acid → methyl (2R)-3-amino-2-methylpropanoate hydrochloride

HRID 725657Notes

Reaction equation

HRID 725657 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@H:4]([CH3:9])[CH2:5][N:6]=[N+]=[N-].[ClH:11]>O1CCCC1.[Pd]>[ClH:11].[CH3:1][O:2][C:3](=[O:10])[C@H:4]([CH3:9])[CH2:5][NH2:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 150729(R)-3-Azido-2-methylpropanoic acid, methyl ester

Product 1

HCID 86749859methyl (2R)-3-amino-2-methylpropanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.7 g of 3-azido-2(R)-methylpropionic acid methyl ester are hydrogenated in the presence of 1.4 g of 10% Pd/C in 50 ml of tetrahydrofuran for 4 hours at room temperature at pH 6.0(pH-stat; 2N hydrochloric acid). The reaction mixture is filtered and concentrated by evaporation. The title compound is obtained by crystallisation from isopropanol/diethyl ether: 1H NMR (DMSO-d6), δ(ppm)=7.95 (3H, bs), 3.65 (3H, s), 3.12-2.78 (3H, m), 1.15 (3H, d); m.p. 122°-125° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fdfc2f9a2ff249bc98a7fe520d0e2839
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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