Sodium Bicarbonate → HCID 178453916, compound

HRID 547372Notes

Reaction equation

HRID 547372 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([F:18])[C:6]2[O:10][N:9]=[C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7]=2[CH:17]=1.[C:19]([O:23][C:24](=[O:35])[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32][CH:33]=O)[CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:19]([O:23][C:24](=[O:35])[NH:25][C@H:26]1[CH2:27][CH2:28][C@H:29]([CH2:32][CH2:33][N:14]2[CH2:13][CH2:12][N:11]([C:8]3[C:7]4[CH:17]=[C:3]([F:2])[CH:4]=[C:5]([F:18])[C:6]=4[O:10][N:9]=3)[CH2:16][CH2:15]2)[CH2:30][CH2:31]1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67130408HCID 67130408, compoundHCID 178453924HCID 178453924, compound

Product 1

HCID 178453916HCID 178453916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution in CH2Cl2 (20 ml) of 5,7-difluoro-3-piperazin-1-yl-benzo[d]isoxazole hydrochloride (1.35 g, 4.9 mmol) and trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1.77 g, 7.3 mmol; prepared according to WO2007/093540) was stirred 15 min at r.t. before addition of Na(AcO)3BH (1.87 g, 8.8 mmol). The reaction mixture was stirred 2 h at r.t., then sat. aq. NaHCO3 was added and the product was extracted with 3 portions of CH2Cl2. After drying (Na2SO4) and evaporation of the solvent the product was purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→90:10) to obtain 2.59 g (quant.) of title compound as a white solid. m/z=465.3 ([M+H]+); 409.3 ([M+H—C4H8]+).

Workup

  1. extractionthe product was extracted with 3 portions of CH2Cl2
  2. customAfter drying
  3. custom(Na2SO4) and evaporation of the solvent the product
  4. customwas purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→90:10)

Sources & evidence

ORD record
ord-74c88e34d3834ad2beb6c1c8d63c5e3f
Source dataset
uspto-grants-2011_05
Patent number
US07939535B2

Reaction notes

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