p-Anisoyl chloride → Benzyl 3-[1-(4-methoxybenzoyl)-5-oxo-2-pyrrolidinyl]propanoate

HRID 1262682Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:18])[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][C:14](=[O:17])[NH:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:8][C:9](=[O:18])[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][C:14](=[O:17])[N:13]1[C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 50 g of 5-oxo-2-pyrrolidinepropanoic acid benzyl ester in 800 ml of tetrahydrofuran is treated with 28.3 g of 4-methoxybenzoyl chloride. The mixture is heated to 55° C. and a solution of 20 g of triethylamine in 400 ml of tetrahydrofuran is added dropwise over a two hour period. The mixture is stirred and heated at 55° C. for 16 hours. The warm mixture is filtered through filter aid to remove triethylamine hydrochloride and concentrated at reduced pressure. Chromatography over silica using a Waters Prep 500 HPLC apparatus yielded 1-(4-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester mp 80°-83° C. After concentration and crystallization.

Workup

temperatureheated at 55° C. for 16 hours
filtrationThe warm mixture is filtered
filtrationthrough filter aid
customto remove triethylamine hydrochloride
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-7d3694fcb23c4a62b03e1667f9a5f78c
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04452990

Reaction notes

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