Sodium Hydroxide → HCID 19854936, compound

HRID 1649848Notes

Reaction equation

C([O:4][C:5]([CH3:36])([CH3:35])[C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)[N:13]=1)=[O:7])(=O)C.[OH-].[Na+]>C(O)C>[OH:4][C:5]([CH3:36])([CH3:35])[C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:20]2)[N:13]=1)=[O:7]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(2-acetoxy-2-methylpropionylamino)-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (1.1 g), 1N sodium hydroxide (2.2 ml) and ethanol (23 ml) was heated at 40° C. with stirring for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was extracted with a mixture of chloroform and methanol (10:1 V/V). The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was pulverized with 70% ethanol and collected by filtration. Recrystallization from 70% ethanol gave 2-(2-hydroxy-2-methylpropionylamino)-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.65 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionthe residue was extracted with a mixture of chloroform and methanol (10:1 V/V)
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off
filtrationcollected by filtration
customRecrystallization from 70% ethanol

Sources & evidence

ORD record: ord-98cd7003fe914b9a814e3c72ac87b37d
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04921887

Reaction notes

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