Water → HCID 87260387, compound

HRID 272282Notes

Reaction equation

HRID 272282 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:53]=[CH:54][CH:55]=1)[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])([CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][OH:24])=[C:15]([Cl:52])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:53]=[CH:54][CH:55]=1)[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:49])[CH3:51])=[O:46])([CH2:25][O:26][Si:27]([C:40]([CH3:42])([CH3:43])[CH3:41])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=[O:24])=[C:15]([Cl:52])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 67076967HCID 67076967, compound

Product 1

HCID 87260387HCID 87260387, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 191 (940 mg) was dissolved in DMF (10 mL). To this solution, pyridinium dichromate (800 mg) was added and the mixture was stirred for 48 hours at room temperature. Following addition of water, the mixture was extracted with ethyl acetate. The extract was then washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate. The solvent was concentrated and the residue was purified on a silica gel chlomatography (hexane:ethyl acetate=3:1) to give the desired product as a colorless oil (710 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was then washed sequentially with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe residue was purified on a silica gel chlomatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-7eec37a6c35d4d31a6c4d925e636db88
Source dataset
uspto-grants-2008_11
Patent number
US07456157B2

Reaction notes

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