HCID 59267990, compound → HCID 59268004, compound

HRID 1802442Notes

Reaction equation

HRID 1802442 reaction equation
[C:1]([Si:5]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:6][CH2:7][C:8]([C:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:32])[C:18]([S:21]([CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)(=[O:23])=[O:22])([CH3:20])[CH3:19])[O:13][N:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[C:1]([Si:5]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:6][CH2:7][C:8]([C:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:32])[C:18]([CH3:20])([S:21]([CH2:24][CH:25]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]2)(=[O:23])=[O:22])[CH3:19])[O:13][N:12]=1)([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 59267990HCID 59267990, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59268004HCID 59268004, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.21 g (0.36 mmol) of N-{3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-(4-hydroxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide in DCM (3 mL) is added pyridinium chlorochromate (0.15 g, 0.72 mmol) and the reaction mixture is stirred at room temperature for 18 h. The reaction is diluted with diethyl ether (6 mL) and stirred for 10 min. The mixture is filtered through a plug of silica and the filtrate is concentrated to afford 0.12 g of N-{3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-methyl-2-(4-oxo-cyclohexylmethanesulfonyl)-propionamide, which is used without further purification in the next step. Yield: 54%, ES-MS: 637 [M−H]

Workup

  1. stirringstirred for 10 min
  2. filtrationThe mixture is filtered through a plug of silica
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-697972ece6754c8290becf33b898e58a
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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