Acetic Acid → HCID 86759800, compound

HRID 584620Notes

Reaction equation

HRID 584620 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C@@H:7]2[CH2:11][NH:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)=[CH:4][CH:3]=1.[O:18]1[CH2:20][CH:19]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:32])[CH3:31].C(O)(=O)C>C(O)(C)(C)C>[ClH:1].[ClH:1].[C:30]([NH:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[O:22][CH2:21][CH:19]([OH:18])[CH2:20][N:10]1[CH2:11][C@@H:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:8][C@H:9]1[C:12]([O:14][CH3:15])=[O:13])(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2796251N-[2-(oxiran-2-ylmethoxy)phenyl]acetamideHCID 26192764(4S)-4-(4-Chlorophenoxy)-L-proline methyl ester

Product 2

HCID 313Hydrochloric AcidHCID 86759800HCID 86759800, compoundYield 216.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl (2S,4S)-4-(4-chlorophenoxy)-2-pyrrolidinecarboxylate (370 mg, 1.0 mmol) and N-[2-(2-oxiranylmethoxy)phenyl]acetamide (207 mg, 1.0 mmol) dissolved in tert-butanol (7 ml) was stirred in a sealed vial at 100° C. over night. Workup of the crude material by flash chromatography on silica (DCM/MeOH 100/2), acidification of the appropriate fractions with 1M HCl and lyophilization from acetic acid afforded the subtitled compound as a white amorphous solid (360 mg, 72%). The substance is a diastereomeric mixture.

Sources & evidence

ORD record
ord-36e094fb7eaf4fa282bd4eb050d0fb5e
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

Loading…