Cyclohexylammonium Ion → HCID 131720684, compound

HRID 962947Notes

Reaction equation

HRID 962947 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8](=[O:25])[C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14](=[O:24])[C@@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:16].[CH:26]1([NH3+:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(OCC)C>[CH:26]1([NH3+:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8](=[O:25])[C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14](=[O:24])[C@@H:15]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:16]

Participants

4

Reactant 2

HCID 1549093Cyclohexylammonium IonHCID 131720685HCID 131720685, compound

Product 1

HCID 131720684HCID 131720684, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.74 g (25 mmole) of O-tetrahydropyranyl-3-phenyl-D-lactic acid cyclohexylammonium salt (Example 5, Step A) is dissolved in 30 ml of 1M potassium hydrogen sulfate and 50 ml of dichloromethane. The dichloromethane layer is washed with water, dried over sodium sulfate and evaporated at 20-25 millibar from a water bath at about 40° C. The obtained O-tetrahydropyranyl-3-phenyl-D-lactic acid and 4.15 g (25 mmole) of L-proline methyl ester hydrochloride are condensed by the method of Obrecht and Heimgartner [Helv. Chim. Acta 67, 526 (1984)], the O-tetrahydropyranyl-3-phenyl-D-lactyl-L-proline methyl ester formed is saponified and the resulting O-tetrahydropyranyl-3-phenyl-D-lactyl-L-proline is converted in diethyl ether solution to the crystalline cyclohexylammonium salt.

Sources & evidence

ORD record
ord-4e5f66b17b8945bf946fa020d2bdd4c8
Source dataset
uspto-grants-1998_06
Patent number
US05760235

Reaction notes

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