tert-Butyldiphenylchlorosilane → HCID 59268006, compound

HRID 553653Notes

Reaction equation

HRID 553653 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:28])[C:13]([S:16]([CH2:19][CH:20]2[CH2:25][CH2:24][CH:23]([O:26][CH3:27])[CH2:22][CH2:21]2)(=[O:18])=[O:17])([CH3:15])[CH3:14])[O:8][N:7]=1)([CH3:5])[CH3:4].[C:29]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])([CH3:31])[CH3:30]>C(Cl)Cl>[C:29]([Si:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[O:1][CH2:2][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:28])[C:13]([S:16]([CH2:19][CH:20]2[CH2:21][CH2:22][CH:23]([O:26][CH3:27])[CH2:24][CH2:25]2)(=[O:18])=[O:17])([CH3:15])[CH3:14])[O:8][N:7]=1)([CH3:4])[CH3:5])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 59267935HCID 59267935, compound

Product 1

HCID 59268006HCID 59268006, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.41 g (0.96 mmol) of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-(4-methoxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide in DCM (8 ml) are added imidazoles (0.07 g, 0.96 mmol), followed by tert-Butylchlorodiphenylsilane (0.26 g, 0.96 mmol). The reaction is stirred at room temperature for 20 h. The mixture is diluted with DCM (10 mL) and washed with saturated aqueous NH4Cl solution, brine, dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure to give 0.73 g of N-{3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-(4-methoxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide. Yield: 100%, ES-MS: 655 [M+H].

Workup

  1. washwashed with saturated aqueous NH4Cl solution, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e97196563f74bda817b726cb78d824f
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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