Sodium Thiosulfate → HCID 71255466, compound

HRID 540279Notes

Reaction equation

HRID 540279 reaction equation
S1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:12]2[CH:21]=[C:20]([CH:22]([OH:36])[CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH3:37])[CH:18]=3)[N:13]=2)[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=O)C=1.[S:49]([O-:53])([O-])(=[O:51])=S.[Na+].[Na+]>ClCCl>[O:51]=[S:49]1(=[O:53])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][N:4]([C:12]2[CH:21]=[C:20]([CH:22]([OH:36])[CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:27][CH2:28]3)[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH3:37])[CH:18]=3)[N:13]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 71255024HCID 71255024, compound

Product 1

HCID 71255466HCID 71255466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{[2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl](hydroxy)methyl}piperidine-1-carboxylate (519 mg, 1.0 mmol) in dichloromethane (10 mL) was added 3-chloroperbenzoic acid (537 mg, 70% purity, 2.2 mmol). After being stirred at room temperature for 4 hours, to the above mixture was added a saturated aqueous solution of sodium thiosulfate (3 mL). The separated organic layer was washed with a saturated aqueous solution of sodium carbonate (5 mL) and brine (5 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluting with 20-50% ethyl acetate in petroleum ether) to afford 300 mg of the desired product. MS (ESI+) [(M+H)+] 552.

Workup

  1. washThe separated organic layer was washed with a saturated aqueous solution of sodium carbonate (5 mL) and brine (5 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (eluting with 20-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-4aeeb6a9bb3747dabd7f41f0aa370b63
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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