L-Threonine → HCID 12881248, compound

HRID 842354Notes

Reaction equation

HRID 842354 reaction equation
S(Cl)([Cl:3])=O.N[C@H](C(O)=O)[C@@H](C)O.[ClH:13].[CH3:14][O:15][C:16](=[O:22])[C@H:17]([C@@H:19]([CH3:21])O)[NH2:18]>CO>[ClH:3].[CH3:14][O:15][C:16](=[O:22])[CH:17]([NH2:18])[CH:19]([Cl:13])[CH3:21]

Participants

5

Reactant 3

HCID 6288L-ThreonineHCID 24386Thionyl Chloride2×HCID 2734893Methyl L-threoninate hydrochloride

Product 1

HCID 12881248HCID 12881248, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using thionyl chloride and methanol, threonine was derivatized into threonine methyl ester hydrochloride, which was then treated with thionyl chloride to give α-amino-β-chlorobutyric acid methyl ester hydrochloride. This was then converted to α-amino-β-chloropropionic acid hydrochloride by hydrolyzing with hydrochloric acid. The α-amino-β-chloropropionic acid hydrochloride was crystallized and isolated by the same technique as mentioned in Example 8.

Sources & evidence

ORD record
ord-1895051c68fd4d468a579f3ab76479ec
Source dataset
uspto-grants-2002_04
Patent number
US06372941B1

Reaction notes

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