Triethyl phosphonoacetate → HCID 57496388, compound

HRID 537748Notes

Reaction equation

HRID 537748 reaction equation
C(OP(CC(OCC)=O)(OCC)=O)C.[H-].[Na+].[F:17][C:18]1([F:46])[CH2:23][CH2:22][CH2:21][CH:20]([C@@H:24]2[CH2:29][C@H:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:27][CH2:26][N:25]2C(OCC2C=CC=CC=2)=O)[CH2:19]1>C1COCC1>[F:46][C:18]1([F:17])[CH2:23][CH2:22][CH2:21][CH:20]([C@@H:24]2[CH2:29][C@H:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:27][CH2:26][NH:25]2)[CH2:19]1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 57496387HCID 57496387, compound

Product 1

HCID 57496388HCID 57496388, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (62.7 g, 0.28 mol) in THF (500 mL) at 0° C. was added NaH (6.77 g, 0.28 mol). After stirring for 1 h, a solution of compound 6 (48 g, 0.16 mol) in THF was added dropwise. The mixture was stirred at room temperature overnight, quenched with water, and extracted with EA. The combined extracts were dried over Na2SO4 and filtered. The filtrate was concentrated and purified on silica gel (PE:EA=30:1) to give 13 g of compound 7 in 30% yields.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched with water
  3. extractionextracted with EA
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified on silica gel (PE:EA=30:1)

Sources & evidence

ORD record
ord-2e19fcbe7aa041009bf9c31f40d6f94e
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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