tert-Butyldiphenylchlorosilane → HCID 59268006, compound

HRID 1802440Notes

Reaction equation

HRID 1802440 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-bb2e665224cf459b935317240118ec0a
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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