Hydrochloric Acid → (2S)-(E)-[4-(2-carboxyethen-1-yl)thiazol-2-ylthio]-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide

HRID 545118Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH:22]=O)[N:21]=2)[CH2:7]1.C(O)(=O)[CH2:30][C:31]([OH:33])=[O:32].N1CCCCC1.Cl>N1C=CC=CC=1.O>[C:31](/[CH:30]=[CH:22]/[C:20]1[N:21]=[C:17]([S:16][CH2:15][C:14]([NH:13][CH2:12][C@@H:8]2[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:25]=[CH:26][C:27]([Cl:28])=[C:2]([Cl:1])[CH:3]=3)[CH2:7]2)=[O:24])[S:18][CH:19]=1)([OH:33])=[O:32]

Participants

Conditions

Temperature: 100 °C

Procedure

The resultant product (643 mg) of (70-2) was dissolved in pyridine (5 mL), malonic acid (291 mg) and piperidine (14 μL) were added, and the mixture was stirred at 100° C. for 3.5 hrs. The reaction mixture was poured into water, 1M hydrochloric acid was added to adjust to pH=4, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (618 mg) as a white amorphous solid.

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography
customThe solvent was evaporated from the eluent

Sources & evidence

ORD record: ord-ca47636c2f274beab94dde1a03579a3b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935700B2

Reaction notes

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