m-Chloroperbenzoic acid → HCID 17848288, compound

HRID 917640Notes

Reaction equation

HRID 917640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:14])=[C:11]([N:26]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]2)[N:10]=[C:9]([S:33][CH3:34])[N:8]=1.ClC1C=CC=C(C(OO)=[O:48])C=1>C(Cl)Cl.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:14])=[C:11]([N:26]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]2)[N:10]=[C:9]([S:33]([CH3:34])=[O:48])[N:8]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 17848323HCID 17848323, compound

Product 1

HCID 17848288HCID 17848288, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-(3-chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-(4-hydroxypiperidin-1-yl)-2-methylthiopyrimidine (prepared in the above (3)) 100 mg in methylene chloride 3 ml is added at room temperature a solution of m-chloroperbenzoic acid 79 mg in methylene chloride 2 ml, and the mixture is stirred for 30 minutes. The reaction mixture is diluted with an aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-(4-hydroxypiperidin-1-yl)-2-methylsulfinylpyrimidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6080394ef9ba41389ba35885ee8eab79
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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