Water → HCID 178441167, compound

HRID 336185Notes

Reaction equation

HRID 336185 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[C:19]([N:21]2[CH2:26][CH2:25][S:24][CH2:23][CH2:22]2)=[O:20])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:27]OS([O-])=O.[K+].O>C(Cl)Cl.CO>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[C:19]([N:21]2[CH2:26][CH2:25][SH2:24](=[O:27])[CH2:23][CH2:22]2)=[O:20])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 70865117HCID 70865117, compound

Product 1

HCID 178441167HCID 178441167, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-(Thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (150 mg; 0.394 mmol) in 50% methylene chloride in methanol (4 mL) is added oxone (122.8 mg; 0.2 mmol) and water (0.1 mL). The reaction mixture is stirred at room temperature for 2 hours. The mixture is quenched with water and extracted with dichloromethane 3 times. The organics are combined and dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 397 [M+H+].

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-28cfa288a9e84c40b8cb70eb00806057
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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