Water → HCID 67185843, compound

HRID 1441961Notes

Reaction equation

HRID 1441961 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11]([O:15][C:16]([NH:18][CH:19](P(OC)(OC)=O)[C:20]([O:22][CH3:23])=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].O.C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6](/[CH:7]=[C:19](\[NH:18][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])/[C:20]([O:22][CH3:23])=[O:21])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 67185843HCID 67185843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

21.32 ml (169.9 mmol) of N,N,N,N-tetramethylguanidine are added to a solution, cooled to −70° C., of 30 g (147.8 mmol) of 5-bromo-2-fluorobenzaldehyde and 50.51 g (169.9 mmol) of methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate in 450 ml anhydrous tetrahydrofuran. After stirring at −70° C. for 4 h, the reaction mixture is stirred at RT for 15 h. 1000 ml of water and 1000 ml of ethyl acetate are added to the mixture. The organic phase is washed with water, dried over sodium sulfate and concentrated. The crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 4:1).

Workup

  1. stirringthe reaction mixture is stirred at RT for 15 h
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-302ddb23e87546b49578655ba631daaf
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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