Water → HCID 69597616, compound

Participants

Reaction Steps

A mixture of [(4-benzyloxy-benzenesulfonyl)-pent-4-enyl-amino]-acetic acid tert-butyl ester (compound of formula XVI, 89 g, 200 mmol), cuprous chloride (19.8 g, 200 mmol), palladium (II) chloride (6.9 g, 39 mmol), dimethylformamide (541 ml) and water (293 ml) was treated with oxygen gas under vigorous stirring. After about 24 hours, an additional 4 g of cuprous chloride and 2 g of palladium (II) chloride were added, and stirring was continued for 2 days. The mixture was diluted with 1M hydrochloric acid, extracted 3 times with ethyl acetate, and the organic phase was washed 5 times with water, dried over sodium sulfate, filtered and concentrated, giving 83 g of [(4-benzyloxy-benzenesulfonyl)-(4-oxo-pentyl)-amino]-acetic acid tert-butyl ester (compound of formula XVII) as a colorless syrup.

Provenance & Evidence