Methanol → (R)-2-Amino-2-methyl-butyric acid methyl ester hydrochloride

HRID 2075534Notes

Reaction equation

HRID 2075534 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@:6]([CH3:12])([CH2:10][CH3:11])[C:7]([OH:9])=[O:8].[CH3:13]O>>[ClH:3].[CH3:13][O:8][C:7](=[O:9])[C@@:6]([NH2:5])([CH3:12])[CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 2724877D-Isovaline

Product 1

HCID 13018906(R)-2-Amino-2-methyl-butyric acid methyl ester hydrochloride

Procedure

Thionyl chloride (0.50 mL) was added dropwise to dry MeOH (2 mL) at −10° C. After stirring at −10° C. for 1 h, a 0° C. solution of (R)-2-amino-2-methyl-butyric acid (0.068 g) in MeOH (1 mL) was added, and the mixture was allowed to warm to room temperature, and was stirred for an additional 24 h. The reaction mixture was concentrated in vacuo, repeatedly diluted with toluene (50 mL) and reconcentrated in vacuo to give 0.076 g (quant. yield) of (R)-2-amino-2-methyl-butyric acid methyl ester hydrochloride as a light yellow solid.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionrepeatedly diluted with toluene (50 mL)

Sources & evidence

ORD record
ord-6bcc5357fb7f49928c2d6cc5a3f7d67e
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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