Ethyl Acetate → 3-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid

HRID 1418332Notes

Reaction equation

HRID 1418332 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][CH2:33][OH:34])[N:18]=[C:17]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:42].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)(=O)C>CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:16]=[C:17]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[N:18]=[C:19]([O:30][CH2:31][CH2:32][C:33]([OH:42])=[O:34])[C:20]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 153811024-t-butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]-benzenesulfonamide

Product 1

HCID 153811033-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acidYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-t-Butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyl]-benzenesulfonamide (800 mg) was dissolved in dimethylformamide (40 ml). Pyridinium dichromate (2.63 g) was added to the solution, and the resultant mixture was stirred for 14 hours at room temperature. Ethyl acetate was added to the reaction mixture, followed by successive washing with 0.5N-HCl, water, and brine. The organic layer was dried over anhydrous sodium sulfate and, evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=25:1), to thereby obtain 128 mg (yield: 16%) of the title compound as a white powder.

Workup

  1. washby successive washing with 0.5N-HCl, water, and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-a2350f2246fb4908bdb47883110a769f
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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