Water → HCID 69597616, compound

HRID 1796796Notes

Reaction equation

HRID 1796796 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])([CH3:4])([CH3:3])[CH3:2].CN(C)C=[O:35].O.O=O>Cl.[Pd](Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:9][CH2:10][CH2:11][C:12](=[O:35])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 977OxygenHCID 6228DimethylformamideHCID 69597625HCID 69597625, compound2×

Product 1

HCID 69597616HCID 69597616, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalyst2×HCID 313Hydrochloric AcidSolvent

Procedure

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.

Workup

  1. waitwas continued for 2 days
  2. extractionextracted 3 times with ethyl acetate
  3. washthe organic phase was washed 5 times with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2fcd429ce5e14c4182a7c0dc87780716
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

Loading…