L-Serine → Methyl 2-amino-3-chloropropanoate hydrochloride
Reaction equation
N[C@H](C(O)=O)CO.[ClH:8].[CH3:9][O:10][C:11](=[O:16])[C@H:12]([CH2:14]O)[NH2:13].P(Cl)(Cl)(Cl)(Cl)[Cl:18]>>[ClH:18].[CH3:9][O:10][C:11](=[O:16])[CH:12]([NH2:13])[CH2:14][Cl:8]Participants
Procedure
The method which comprises derivatizing a β-hydroxy-α-aminocarboxylic acid into the corresponding β-hydroxy-α-aminocarboxylic acid ester, then halogenating the hydroxyl group thereof with a phosphorus halide to give the corresponding β-halogeno-α-aminocarboxylic acid ester, and hydrolyzing the ester group using a hydrohalogenic acid to give the objective β-halogeno-α-aminocarboxylic acid. Specifically, serine is derivatized into serine methyl ester hydrochloride, the ester salt is then treated with phosphorus pentachloride to give α-amino-β-chloropropionic acid methyl ester hydrochloride, which is further hydrolyzed with hydrochloric acid. The resulting α-amino-β-chloropropionic acid hydrochloride is isolated by concentrating the reaction mixture to dryness, followed by crystallization of the residue from a mixture of 1-propanol and hydrochloric acid [e.g. CHIRALITY, 8:197-200 (1996)]; and
Sources & evidence
- ORD record
- ord-f682234b722e4b21b0266b8d4ce7d29e
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372941B1
Reaction notes
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