1,1,3,3-Tetramethylguanidine → HCID 58868869, compound

HRID 1441960Notes

Reaction equation

HRID 1441960 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][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].CC(C)=O.C(=O)=O.CN(C)C(N(C)C)=N>C1COCC1>[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][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH:9]=1

Participants

6

Reactant 4

HCID 664601,1,3,3-TetramethylguanidineHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 11462935HCID 11462935, compoundHCID 18522661Acetone cardice

Product 1

HCID 58868869HCID 58868869, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (30 mmol) of 5-bromo-2-fluorobenzaldehyde and 12.7 g (34 mmol) of benzyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate are introduced into 90 ml of THF and, while cooling with acetone/dry ice at −78° C., 3.91 g (34 mmol) of 1,1,3,3-tetramethylguanidine are added. After 4 h in the cold bath, the mixture is slowly warmed to RT and stirred at RT for a further 12 h. The solvent is distilled off in vacuo, and the crude product is taken up in ethyl acetate and washed once each with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and evaporated to dryness in vacuo. The crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 2:1).

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. washwashed once each with a saturated sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness in vacuo
  5. customThe crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-db1dae19b8b9461e93a854fe93f48a5b
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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