Water → HCID 10208935, compound

HRID 1871347Notes

Reaction equation

HRID 1871347 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:35]=[CH:34][CH:33]=[CH:32][C:8]=2[C:9]=1[CH2:10][CH2:11][C:12]1[CH:31]=[CH:30][C:15]([O:16][S:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([OH:29])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[C:36](OC(=O)C)(=[O:38])[CH3:37].O>CCOC(C)=O.CN(C)C1C=CN=CC=1>[C:36]([O:29][C:22]1[CH:21]=[C:20]([S:17]([O:16][C:15]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]3[C:8]4[CH:32]=[CH:33][CH:34]=[CH:35][C:7]=4[O:6][C:5]=3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:31][CH:30]=2)(=[O:18])=[O:19])[CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 9827065HCID 9827065, compound

Product 1

HCID 10208935HCID 10208935, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

At ambient temperature, to a stirred solution containing 4-{4-[2-(2-butyl-benzofuran-3-yl)-ethyl]-phenoxysulfonyl}-2-hydroxy-benzoic acid (0.298 g, 0.602 mmol) and acetic anhydride (1 mL) In EtOAc (2 mL) was added 4-(dimethylamino)pyridine (3.7 mg, 0.0301 mmol). The reaction was refluxed for 72 h. The reaction was cooled to ambient temperature, hydrolyzed with H2O (5 mL) and stirred for 24 h. The reaction was diluted with EtOAc and the organic phase washed sequentially with H2O (2×), brine (2×), dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated silica gel, eluting with a 10 & 20% EtOAc/pet ether step gradient gave 0.122 g (76%) of the title compound as a yellow solid, mp 54-57° C. 1H NMR consistent. IR (KBr) 3400, 2900, 1700, 1380 and 1190 cm-1. mass spectrum (-ESI) m/z 535 (M-H).

Workup

  1. temperatureThe reaction was refluxed for 72 h
  2. washthe organic phase washed sequentially with H2O (2×), brine (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on 2% H3PO4 /MeOH
  6. additiontreated silica gel
  7. washeluting with a 10 & 20% EtOAc/pet ether step gradient

Sources & evidence

ORD record
ord-c6285d434cf54b03b5ca52c1fa34aae8
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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