Acetic Anhydride → HCID 68625913, compound

HRID 1819945Notes

Reaction equation

HRID 1819945 reaction equation
[C:1]([O:5][C:6](=[O:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].[CH2:9]([C:11]([C:29]1[S:33][C:32]([S:34]([NH2:37])(=[O:36])=[O:35])=[C:31]([CH3:38])[CH:30]=1)([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([CH3:28])[CH:15]=1)[CH2:12][CH3:13])[CH3:10].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CC(OC(C)=O)=O>ClCCl>[C:1]([O:5][C:6](=[O:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:23]([CH3:24])([CH3:25])[C:22](=[O:27])[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]([C:29]2[S:33][C:32]([S:34]([NH2:37])(=[O:36])=[O:35])=[C:31]([CH3:38])[CH:30]=2)([CH2:9][CH3:10])[CH2:12][CH3:13])=[CH:15][C:16]=1[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 2724130Cornforth reagentHCID 68625053HCID 68625053, compound

Product 1

HCID 68625913HCID 68625913, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid tert-butyl ester (360 mg, 0.63 mmol), pyridinium dichromate (179 mg, 0.48 mmol) and Ac2O (66 μL, 0.7 mmol) in dichloromethane (10 ml) is refluxed for 3 h. The reaction is concentrated and chromatographed (Hex to 15% EtOAc/Hex) to give the title compound (330 mg, 92%); 1H NMR (CDC3): δ 6.96, 7.23 (m, 2H), 6.56 (s, 1H), 6.51 (d, 1H, J=8.3 Hz), 6.57 (s, 1H), 5.08 (t, 1H), 4.85 (s, 2H), 3.71 (d, 2H, J=5.4 Hz), 2.40 (s, 3H), 2.26 (s, 3H), 2.07 (q, 4H), 1.40 (s, 9H), 1.26 (s, 9H), 0.90 (s, 9H), 0.70 (t, 6H);

Workup

  1. temperatureis refluxed for 3 h
  2. concentrationThe reaction is concentrated
  3. customchromatographed (Hex to 15% EtOAc/Hex)

Sources & evidence

ORD record
ord-f5997e0af3d94b4cbca2f5296f6a5a6b
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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