Triethylamine → 1-(3-Benzyloxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester

HRID 1262683Notes

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.[CH2:19]([O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:27]([O:26][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 13 g of 5-oxo-2-pyrrolidinepropanoic acid benzyl ester in 250 ml of tetrahydrofuran is treated with 14.0 g of 3-benzyloxy-4-methoxybenzoyl chloride. The mixture is heated to 55° C. and a solution of 5.5 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 yields 1-(3-benzyloxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester with mp 92°-95° 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-1543ed88c6a54ce18a7c083d389d1894
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04452990

Reaction notes

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