Water → HCID 67106218, compound

HRID 1879410Notes

Reaction equation

HRID 1879410 reaction equation
[CH3:1][C:2]1[C:19]([CH3:20])=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[C:4]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)(=[O:24])=[O:23])[CH:3]=1.Br[CH2:32][C@@H:33]([CH3:53])[CH2:34][O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Si:36]([O:35][CH2:34][C@H:33]([CH3:53])[CH2:32][N:21]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)(=[O:23])=[O:24])[C:4]1[CH:3]=[C:2]([C:1]2[CH:18]=[CH:19][CH:2]=[CH:3][CH:4]=2)[C:19]([C:20]2[CH:16]=[CH:17][CH:8]=[CH:9][CH:10]=2)=[CH:18][C:5]=1[O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57063581HCID 57063581, compoundHCID 67107091HCID 67107091, compound

Product 1

HCID 67106218HCID 67106218, compoundYield 139.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

596 mg of methyl 4-({4,5-dimethyl-2-[(pyridin-2-ylsulfonyl)amino]phenoxy}methyl)benzoate was dissolved in 5.96 mL of DMF, and 820 mg of {[(2S)-3-bromo-2-methylpropyl]oxy}(tert-butyl)diphenylsilane and 1.37 g of cesium carbonate were added thereto, followed by stiffing at 80° C. for 4 hours. To the reaction liquid was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40) to obtain 840 mg of methyl 4-[(2-{[(2R)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropyl](pyridin-2-ylsulfonyl)amino}-4,5-diphenylphenoxy)methyl]benzoate.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40)

Sources & evidence

ORD record
ord-7b51561576a04f6ebd73a342d1f26202
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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