Acetic Anhydride → HCID 10282528, compound

HRID 1841349Notes

Reaction equation

HRID 1841349 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:41])=[C:11]([CH3:40])[C:12]=1[C:13]([C:15]1[CH:34]=[CH:33][C:18]([O:19][S:20]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25]([OH:32])[CH:24]=2)(=[O:22])=[O:21])=[C:17]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42](OC(=O)C)(=[O:44])[CH3:43].[I-].[Mg+2].[I-]>CCOCC>[C:42]([O:32][C:25]1[CH:24]=[C:23]([S:20]([O:19][C:18]2[CH:33]=[CH:34][C:15]([C:13]([C:12]3[C:11]([CH3:40])=[C:10]([CH3:41])[O:9][C:8]=3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:14])=[CH:16][C:17]=2[CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)(=[O:22])=[O:21])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 10281572HCID 10281572, compound

Product 1

HCID 10282528HCID 10282528, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution containing 4-[4-(2-benzyl-4,5-dimethyl-furan-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.235 g, 0.409 mmol), acetic anhydride (3.3 mL) and magnesium iodide (0.113 g, 0.409 mmol) in ether (8 mL) was refluxed for 0.5 h. The reaction was allowed to cool to ambient temperature, quenched with H2O (100 mL), extracted with ether and concentrated. The mixed anhydride/product was dissolved in THF (6 mL), treated with H2O (6 mL) and refluxed for 0.5 h. The reaction was allowed to cool to ambient temperature, quenched with H2O (100 mL), extracted with ether and concentrated. Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 18 & 25% EtOAc/pet ether step gradient followed by crystallization from acetone/hexane gave 0.201 g (80%) of the title compound as an off white solid, mp 55-90° C. 1H NMR (DMSO-d6) δ1.23-1.32 (m, 2 H), 1.50-1.53 (m, 2 H), 1.64-1.72 (m, 4 H), 1.76 (s, 3 H), 2.17 (s, 3 H), 2.23 (s, 3 H), 2.92 (quintet, 1 H), 3.79 (s, 2 H), 6.98-7.00 (m, 2 H), 7.15-7.23 (m, 4 H), 7.53 (dd, 1 H), 7.58 (d, 1 H), 7.84 (d, 1 H), 7.88 (dd, 1 H), 8.12 (d, 1 H) 13.7 (br s, 1 H). mass spectrum (−ESI) m/z 615 (M−H). Anal. Calcd. for C34H32O9S .0.5H2O: C, 65.27; H, 5.32; N, 0.00. Found: C, 65.33; H, 5.30; N, 0.03.

Workup

  1. temperaturewas refluxed for 0.5 h
  2. customquenched with H2O (100 mL)
  3. extractionextracted with ether
  4. concentrationconcentrated
  5. dissolutionThe mixed anhydride/product was dissolved in THF (6 mL)
  6. additiontreated with H2O (6 mL)
  7. temperaturerefluxed for 0.5 h
  8. temperatureto cool to ambient temperature
  9. customquenched with H2O (100 mL)
  10. extractionextracted with ether
  11. concentrationconcentrated
  12. customPurification on 2% H3PO4/MeOH
  13. additiontreated silica gel
  14. washeluting with a 18 & 25% EtOAc/pet ether step gradient
  15. customfollowed by crystallization from acetone/hexane

Sources & evidence

ORD record
ord-e5cac49572654917a10bacc25ef28571
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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