m-Chloroperbenzoic acid → (1S,4S)-tert-Butyl 5-(3-(methylsulfinyl)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 630505Notes

Reaction equation

HRID 630505 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:30][C@@H:29]4[CH2:31][C@H:26]3[CH2:27][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:24])=[CH:20][CH:21]=2)[N:16]([C:39]2[N:44]=[CH:43][C:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:41][N:40]=2)[CH:15]=1>ClCCl>[CH3:12][S:13]([C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:30][C@@H:29]4[CH2:31][C@H:26]3[CH2:27][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])=[O:24])=[CH:20][CH:21]=2)[N:16]([C:39]2[N:44]=[CH:43][C:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:41][N:40]=2)[CH:15]=1)=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131735400(1S,4S)-tert-Butyl 5-(3-(methylthio)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 131735399(1S,4S)-tert-Butyl 5-(3-(methylsulfinyl)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperoxybenzoic acid (0.114 g, 0.66 mmol, 0.9 eq) was added at 0° C. to a stirred solution of 244c) (0.400 g, 0.61 mmol, 1 eq) in dichloromethane (30 mL). The reaction mixture was stirred for 3 h at room temperature, then diluted with dichloromethane (50 mL) and successively washed with saturated sodium hydrogen carbonate solution (2×30 mL) and brine (30 mL). The organic layer wasdried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography [230-400 mesh silica gel, dichloromethane/methanol=95:5]. White solid. Yield: 0.290 g (71% of theory)

Workup

  1. washsuccessively washed with saturated sodium hydrogen carbonate solution (2×30 mL) and brine (30 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography [230-400 mesh silica gel, dichloromethane/methanol=95:5]

Sources & evidence

ORD record
ord-b1fa3380ec3f410aaf6f7f17ceabbb52
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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