Water → HCID 131734291, compound

HRID 1502007Notes

Reaction equation

HRID 1502007 reaction equation
[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@@H:10]2S[CH2:14][C@@H:13]3[CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][N:12]3[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].O[O:29][S:30]([O-:32])=O.[K+].[OH2:34]>C(#N)C.ClCCl>[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@@H:10]2[S:30](=[O:32])(=[O:29])[CH2:14][C@@H:13]3[CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][N+:12]3([O-:34])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 89619176(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate

Product 1

HCID 131734291HCID 131734291, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate (20 mg, 0.051 mmol) was dissolved in acetonitrile (0.5 mL) and water (0.2 ml) and cooled to 0° C. OXONE (86.1 mg, 0.140 mmol) was added. The ice bath was removed and the reaction mixture was stirred at room temperature overnight. LC-MS showed the completion of the reaction. The reaction mixture was diluted with dichloromethane and water. The organic layer was separated and the aqueous layer was extracted with DCM again. The organic layers were combined and washed with brine, dried (Na2SO4) and concentrated: LC-MS: M+1=440, M+41=481.

Workup

  1. customThe ice bath was removed
  2. customthe completion of the reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM again
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b1390acf021a443fab6e28aebd084068
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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