Acetic Acid → HCID 68093007, compound

HRID 402822Notes

Reaction equation

HRID 402822 reaction equation
Cl.[O:2]=[C:3]1[N:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[CH2:6][C:5]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:4]1.C([BH3-])#N.[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=O.CC(O)=O>CN(C=O)C>[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][C:36]([F:37])([F:38])[F:39])[CH2:30][N:20]1[CH2:21][CH2:22][C:5]2([O:4][C:3](=[O:2])[N:7]([C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)[CH2:6]2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 131504163-Bromo-4-(trifluoromethoxy)benzaldehydeHCID 66764605Methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate hydrochloride salt

Product 1

HCID 68093007HCID 68093007, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate hydrochloride salt (300 mg, 0.918 mmol; Example 1, Step 2), MP-cyanoborohydride (1192 mg, 2.75 mmol), 3-bromo-4-trifluoromethoxybenzaldehyde (272 mg, 1.01 mmol) and AcOH (79 μl, 1.38 mmol) was added 5 mL of DMF. The reaction mixture was filtered, the resin was washed with DMF and the solvent was evaporated. The residue was dissolved in saturated aqueous NaHCO3 and extracted with DCM. The combined organic layers were evaporated to yield the title compound as a light yellow solid (330 mg) that was used without any further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resin was washed with DMF
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in saturated aqueous NaHCO3
  5. extractionextracted with DCM
  6. customThe combined organic layers were evaporated

Sources & evidence

ORD record
ord-099dc13b5d0f450fa14b0efad44ceab4
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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