Ammonium Chloride → HCID 66658219, compound

HRID 420607Notes

Reaction equation

HRID 420607 reaction equation
C[O:2][C:3]([C@H:5]1[N:10]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:9][CH2:8][N:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6]1)=O.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[C:27]([O:26][C:24]([N:7]1[CH2:8][CH2:9][N:10]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:17]=[CH:16][C:14]=3[N:15]=2)[C@H:5]([CH2:3][OH:2])[CH2:6]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 66657879HCID 66657879, compound

Product 1

HCID 66658219HCID 66658219, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1,3-dicarboxylic acid-1-t-butyl ester-3-methyl ester (1.18 g) in tetrahydrofuran (10 mL) was added lithium borohydride (65.7 mg). The mixture was stirred for 20 hours. To the reaction solution was added aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (840 mg). Yield: 76%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-0b543b8e2aa84afca285d849fd24f254
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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