HCID 15004123, compound → HCID 15004128, compound

HRID 1742127Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17]COC(=O)C(C)(C)C)=[O:16])=[C:13]([CH3:26])[N:12]([CH2:27][O:28][CH3:29])[C:11]([CH3:30])=[C:10]1[C:31]([O:33][CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:32]>C(OC(C)C)(C)C.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:31]([O:33][CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:38])([CH3:39])[CH3:40])=[O:32])=[C:11]([CH3:30])[N:12]([CH2:27][O:28][CH3:29])[C:13]([CH3:26])=[C:14]1[C:15]([OH:17])=[O:16]

Participants

Conditions

Temperature: 25 °C

Procedure

In 15 ml of isopropyl ether saturated with water was dissolved 614 mg of bis(pivaloyloxymethyl) 4-(2,3-dichloro-phenyl)-1,4-dihydro-2,6-dimethyl-l-methoxymethyl-3,5-pyridinedicarboxylate obtained in Example 6, and 100 mg of Lipase B was added thereto, followed by stirring at 25° C. for 4 hours. Any insoluble matter was removed by filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 405 mg (yield: 81%) of (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-1-methoxymethyl-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid as a colorless crystal.

Workup

additionwas added
customAny insoluble matter was removed by filtration
washwashed with dichloromethane
concentrationThe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record: ord-e4d407cc4c48472ba25419440f02ab71
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05336774

Reaction notes

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