Sodium Hydroxide → HCID 178433444, compound

HRID 1855401Notes

Reaction equation

Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].CC(C)([O-])C.[K+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:23](=O)[CH2:24][C:25](OC)=[O:26])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[OH-].[Na+]>CO.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([C:23]3[N:5]=[C:2]([CH3:3])[N:4]=[C:25]([OH:26])[CH:24]=3)[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of acetamidine hydrochloride (0.617 g, 6.53 mmol) in methanol (10 mL) was added potassium tert.-butoxide (0.80 g, 6.54 mmol) followed by methyl 3-[1-(4-chlorophenyl)cyclobutyl]-3-oxopropionate (1.34 g, 5.02 mmol). The mixture was stirred at 20° C. for 16 h, then refluxed for 2 h. The reaction mixture was cooled, diluted with water, made alkaline by the addition of 10 mL of 10% aqueous sodium hydroxide solution, and then washed with diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid, and then extracted with diethyl ether. This ether extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (1.04 g, 75%) as a solid foam. Mp 130-140° C.

Workup

temperaturerefluxed for 2 h
temperatureThe reaction mixture was cooled
washwashed with diethyl ether
extractionextracted with diethyl ether
extractionThis ether extract
washwas washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-79a6dfa51d9243b9b73c27f7bedd0f3a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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