(R)-2-Amino-2-methyl-butyric acid methyl ester hydrochloride → (R)-Methyl 2-amino-2-methylbutanoate

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:10])[C@@:5]([CH3:9])([CH2:7][CH3:8])[NH2:6].ClCC(=O)[C@](NC(=O)C1C=C(Cl)C(C)=C(Cl)C=1)(CC)C>>[CH3:2][O:3][C:4](=[O:10])[C@@:5]([CH3:9])([CH2:7][CH3:8])[NH2:6]

Participants

Reactant 2

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

HCID 543167923,5-dichloro-N-[(3R)-1-chloro-3-methyl-2-oxopentan-3-yl]-4-methylbenzamide

Product 1

HCID 7144315(R)-Methyl 2-amino-2-methylbutanoate

Procedure

The (R)-isovaline methyl ester hydrochloride may be converted to (R)-N-(3-chloro-1-ethyl- 1-methyl-2-oxopropyl)-3,5-dichloro-4-methylbenzamide (mp. 155.5-156° C., [α]D=+4.14 in ethanol) using the above-described sequence for preparation of the (S)-enantiomer.

Workup

customfor preparation of the (S)-enantiomer

Sources & evidence

ORD record: ord-825ca944dcd54cac9f4921afda03e388
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566403B1

Reaction notes

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