Ammonium Chloride → HCID 178482534, compound

HRID 493718Notes

Reaction equation

HRID 493718 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[S:4]/[C:3]/1=[N:20]\[CH3:21].C([Li])CCC.[Cl-].[NH4+].[C:29](=O)(O)[O-:30].[Na+]>C1COCC1.C(OCC)(=O)C.CN(C=O)C.CCCCCC>[CH:29]([C:6]1[N:2]([CH3:1])/[C:3](=[N:20]/[CH3:21])/[S:4][C:5]=1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]1)=[O:30]

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 178418339ButyllithiumHCID 178482535HCID 178482535, compound

Product 1

HCID 178482534HCID 178482534, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-5-yl)piperidine-1-carboxylate (5.0 g) obtained in Example 46a) in THF (75 mL) was added n-butyllithium (24 mL, a 1.6 M hexane solution) at −78° C. The reaction solution was mixed for 15 minutes, and then DMF (5 mL) was added thereto, and the mixture was further mixed for 30 minutes. To the reaction solution was added a saturated aqueous ammonium chloride solution, and then poured into a mixed solution of ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was collected by separation, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (3.45 g) as a yellow solid.

Workup

  1. customat −78° C
  2. additionThe reaction solution was mixed for 15 minutes
  3. additionthe mixture was further mixed for 30 minutes
  4. customThe organic layer was collected by separation
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-af3a46d729114369825446ae423a1917
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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