Acetic Anhydride → HCID 18385630, compound

HRID 2298318Notes

Reaction equation

HRID 2298318 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:26](OC(=O)C)(=[O:28])[CH3:27].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[C:26]([NH:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13](=[O:18])[C:12]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4])(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9841854Polmacoxib

Product 1

HCID 18385630HCID 18385630, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

360 mg of 5-{4-(aminosulfonyl)phenyl}-2,2-dimethyl-4-(3-fluorophenyl)-3(2H)-furanone (Example 129) in 30 ml in dichloromethane was reacted with 0.8 ml acetic anhydride in the presence of 0.5 ml triethylamine and 50 mg of 4-(N,N-dimethylamino)pyridine at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, which was followed by extraction with 30 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and then was purified by column chromatography (hexane/ethylacetate 2:1) to afford 397 mg of 5-[4-{(acetylamino)sulfonyl}phenyl]-2,2-dimethyl-4-(3-fluoro-phenyl)-3(2H)-furanone as a solid. mp: 178-179° C. NMR: δ1.57 (s, 6H), 2.08 (s, 3H), 7.05 (m, 3H), 7.34 (m, 1H), 7.82 (d, J=8.4 Hz, 2H), 8.05 (d, J=8.4 Hz, 2H), 8.20 (br s, 1H). IR (cm−1): 3238, 3198, 1431, 1261, 1159.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, which
  2. extractionwas followed by extraction with 30 ml water and dichloromethane (30 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/ethylacetate 2:1)

Sources & evidence

ORD record
ord-da664ebce1944137b84711e30297d353
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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