m-Chloroperbenzoic acid → tert-Butyl 4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfinyl)piperidine-1-carboxylate

HRID 906460Notes

Reaction equation

HRID 906460 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Si:12]([O:19][CH2:20][C:21]([CH3:63])([CH3:62])[CH2:22][N:23]1[CH:32]=[C:31]([S:33][CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]2)[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:47]3[CH:52]=[C:51]([C:53](=[O:58])[NH:54][CH:55]4[CH2:57][CH2:56]4)[CH:50]=[C:49]([F:59])[C:48]=3[CH3:60])[CH:29]=2)[C:24]1=[O:61])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:19][CH2:20][C:21]([CH3:63])([CH3:62])[CH2:22][N:23]1[CH:32]=[C:31]([S:33]([CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]2)=[O:9])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:47]3[CH:52]=[C:51]([C:53](=[O:58])[NH:54][CH:55]4[CH2:56][CH2:57]4)[CH:50]=[C:49]([F:59])[C:48]=3[CH3:60])[CH:29]=2)[C:24]1=[O:61])([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67391538Tert-butyl 4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfanyl)piperidine-1-carboxylate

Product 1

HCID 86640973tert-Butyl 4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfinyl)piperidine-1-carboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (0.025 g of 77% Max) was added to a solution of tert-butyl 4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfanyl)piperidine-1-carboxylate (Example 58d, 0.1 g) in DCM (2 mL). The reaction was stirred at room temperature for 1 h. The reaction was washed with saturated NaHCO3 solution (3×5 mL), then brine (3×5 mL). The organic layer was concentrated under reduced pressure to give the subtitle compound (0.060 g).

Workup

  1. washThe reaction was washed with saturated NaHCO3 solution (3×5 mL)
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b46bbc6ba61e4a3a8f1ec7b6b834c742
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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