3,5-Difluorobenzaldehyde → HCID 14861157, compound

HRID 1062329Notes

Reaction equation

HRID 1062329 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](F)[CH:9]=1)[CH:5]=O.[CH2:11]([O:18][C:19]([NH:21][CH:22](P(OC)(OC)=O)[C:23]([O:25][CH3:26])=[O:24])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][C:19]([NH:21]/[C:22](=[CH:5]\[C:4]1[CH:7]=[CH:8][CH:9]=[CH:2][CH:3]=1)/[C:23]([O:25][CH3:26])=[O:24])=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 5881603,5-DifluorobenzaldehydeHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate

Product 1

HCID 14861157HCID 14861157, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A well stirred solution of 3,5-difluorobenzaldehyde (1.92 g, 13.5 mmol) and methyl benzyloxycarbonylamino-(dimethoxyphosphoryl)acetate (5.37 g, 16.2 mmol) in dry THF (20 mL), under N2, was cooled to 0° C. and 1,1,3,3-tetramethylgaunidine (1.38 g, 16.2 mmol) added via syringe. The reaction was allowed to warm to rt and stir for 6 h, quenched with saturated ammonium chloride and extracted with ethyl acetate. After concentration, the residue was chromatographed on silica gel (elution with 20% ethyl acetate/heptane) to give methyl (Z)-2-benzyloxycarbonylamino-3-phenyl-acrylate (3.55 g) as a white solid. MS (ESI+) for C18H15F2NO4 m/z 348.2 (M+H)+.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentration
  4. customthe residue was chromatographed on silica gel (elution with 20% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3d52177ebfa8433eb06dea86232ab4b9
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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