Methanol → Methyl 3-cyclohexyl-D-alaninate--hydrogen chloride (1/1)

HRID 1417166

Reaction equation

HRID 1417166 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.[CH3:18]O>>[NH2:5][C@@H:6]([C:14]([O:16][CH3:18])=[O:15])[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[ClH:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 56777007(R)-2-Amino-3-cyclohexylpropanoic acid hydrochloride

Product 1

HCID 56777179Methyl 3-cyclohexyl-D-alaninate--hydrogen chloride (1/1)Yield 95.8%

Procedure

To cold (-20° C.) and dry methanol (195 ml) was added dropwise thionylchloride (28 ml). H-D-ChaOH.HCl (40 g) was added and the reaction mixture was heated under reflux for 5 h. The mixture was concentrated in vacuo and coevaporated with methanol (3 times). The residue was crystallized from methanol/diethylether yielding H-D-Cha-OMe.HCl as a white crystalline powder (40.9 g, 95.8%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was crystallized from methanol/diethylether

Sources & evidence

ORD record
ord-8746ba7d899047db9e48974f2f3fec94
Source dataset
uspto-grants-1999_03
Patent number
US05877156

Linked notes

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