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

HRID 324267

Reaction equation

HRID 324267 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)

Procedure

To cold (−20° C.) and dry methanol (195 ml) was added dropwise thionylchloride (28 ml). H—D—Cha—OH.HCl (40 g) was added and the reaction mixture was heated under reflux for 5 hours The mixture was concentrated in vacuo and coevaporated with methanol (3 times). The residue was crystallized from methanol/diethyl ether yielding H—D—Cha—OMe.HCl as a white crystalline powder (40.9 g). TLC: Rf=0.66, silica gel, n-butanol/acetic acid/water 10/1/3 v/v/v.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 hours The mixture
  3. concentrationwas concentrated in vacuo
  4. customThe residue was crystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-0cd394abdff64075b31e61d342bdef49
Source dataset
uspto-grants-2001_04
Patent number
US06218365B1

Linked notes

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