Bromhydrol → HCID 59267990, compound

HRID 1809444Notes

Reaction equation

HRID 1809444 reaction equation
[Br-].[Br-].[Br-].[Al+3].[C:5]([Si:9]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[O:10][CH2:11][C:12]([C:15]1[CH:19]=[C:18]([NH:20][C:21](=[O:37])[C:22]([S:25]([CH2:28][CH:29]2[CH2:34][CH2:33][CH:32]([O:35]C)[CH2:31][CH2:30]2)(=[O:27])=[O:26])([CH3:24])[CH3:23])[O:17][N:16]=1)([CH3:14])[CH3:13])([CH3:8])([CH3:7])[CH3:6]>C(S)C>[C:5]([Si:9]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:10][CH2:11][C:12]([C:15]1[CH:19]=[C:18]([NH:20][C:21](=[O:37])[C:22]([S:25]([CH2:28][CH:29]2[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]2)(=[O:27])=[O:26])([CH3:24])[CH3:23])[O:17][N:16]=1)([CH3:14])[CH3:13])([CH3:6])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 59268006HCID 59268006, compound

Product 1

HCID 59267990HCID 59267990, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent2×

Procedure

In a round bottom flask, aluminium tribromide (0.59 g, 2.2 mmol) is added portionwise to ethanethiol (3 mL), followed by a solution of 0.72 g (1.1 mmol) of N-{3-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-(4-methoxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide in ethanethiol (4 mL). The reaction mixture is stirred at room temperature for 1 h. The reaction is quenched by addition of 4M aqueous HCl solution (2 mL), diluted with ice water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic extracts are washed with brine, dried (MgSO4), filtered and the solvent is removed under reduced pressure. The residue is dissolved (DCM, 20% ethyl acetate) and filtered through a plug of silica to remove colouration and the filtrate is concentrated under reduced pressure to give 0.21 g of N-{3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-(4-hydroxy-cyclohexylmethanesulfonyl)-2-methyl-propionamide which is used in the next step without further purification. Yield: 33%, ES-MS: 639 [M−H]

Workup

  1. customThe reaction is quenched by addition of 4M aqueous HCl solution (2 mL)
  2. additiondiluted with ice water (10 mL)
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. dissolutionThe residue is dissolved (DCM, 20% ethyl acetate)
  9. filtrationfiltered through a plug of silica
  10. customto remove colouration
  11. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c214eaa77fd34f0c9ff2f486d75760cd
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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