Potassium peroxymonosulphate → HCID 70654860, compound

HRID 2178189Notes

Reaction equation

HRID 2178189 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C@:8]2([CH:16]([F:18])[F:17])[CH2:14][CH2:13]S[CH2:11][C:10]([NH2:15])=[N:9]2)[CH:7]=1.[S:20]([O-:25])(O[O-])(=O)=[O:21].[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C@:8]2([CH:16]([F:17])[F:18])[CH2:14][CH2:13][S:20](=[O:25])(=[O:21])[CH2:11][C:10]([NH2:15])=[N:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 10313463Potassium peroxymonosulphateHCID 70654348HCID 70654348, compound

Product 1

HCID 70654860HCID 70654860, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-2,5,6,7-tetrahydro-[1,4]thiazepin-3-ylamine (364 mg, 1.03 mmol) in methanol (20 ml) was treated in two portions with potassium peroxymonosulfate (Oxone) (1.27 g, 2.06 mmol) at 23° C. The white suspension was stirred at 23° C. for 5 hours. For the workup, the reaction mixture was quenched at 0° C. under vigorous stirring with water (10 ml), then treated with a diluted solution of sodium hydrogensulfite, a saturated solution of sodium and with dichloromethane. The vigorous stirring was continued for 10 minutes. The organic layer was separated, washed with water, dried over sodium sulfate and evaporated to give a colorless oil. The crude product was purified by chromatography on silica gel using a gradient of dichloromethane and methanol 100:0 to 90:10 as the eluent. The (S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-ylamine (322 mg, 81% yield) was obtained as a white solid. MS (ISP): m/z=384.9 [M+H]+and =386.9 [M+2+H]+.

Workup

  1. customFor the workup, the reaction mixture was quenched at 0° C.
  2. stirringunder vigorous stirring with water (10 ml)
  3. additiontreated with a diluted solution of sodium hydrogensulfite
  4. stirringThe vigorous stirring
  5. waitwas continued for 10 minutes
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customto give a colorless oil
  11. customThe crude product was purified by chromatography on silica gel using a gradient of dichloromethane and methanol 100:0 to 90:10 as the eluent

Sources & evidence

ORD record
ord-f0e633d46bcf40bba2b78b31564f742e
Source dataset
uspto-grants-2015_06
Patent number
US09067924B2

Reaction notes

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