Methanol → Methyl 3-[6-(4-t-butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionate

HRID 1418355Notes

Reaction equation

HRID 1418355 reaction equation
[CH3:1]O.S(=O)(=O)(O)O.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[N:27]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:25]=[C:24]([O:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[C:23]=2[O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])(=[O:20])=[O:19])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]>O>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:21][C:22]2[N:27]=[C:26]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[N:25]=[C:24]([O:34][CH2:35][CH2:36][C:37]([O:39][CH3:1])=[O:38])[C:23]=2[O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])(=[O:20])=[O:19])=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 153811033-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid

Product 1

HCID 54057768Methyl 3-[6-(4-t-butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (0.5 ml) and concentrated sulfuric acid (two droplets) were added to 3-[6-(4-t-butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid (50 mg), and the mixture was stirred for 4 hours at room temperature, then poured into water, and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel preparative thin layer chromatography (chloroform-methanol (30:1)), to thereby obtain 46 mg (yield: 90%) of the title compound as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel preparative thin layer chromatography (chloroform-methanol (30:1))

Sources & evidence

ORD record
ord-3dd2cc6a5c134cb8848ca00cf6a8c76f
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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