Triethyl phosphonoacetate → HCID 67296271, compound

HRID 2276834Notes

Reaction equation

HRID 2276834 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[C:17]([O:21][C:22](=[O:49])[N:23]([C@H:36]1[CH2:40][CH2:39][C@@H:38]([C:41]2[CH:46]=[CH:45][C:44]([CH:47]=O)=[CH:43][CH:42]=2)[CH2:37]1)[C@@H:24]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:25])([CH3:20])([CH3:19])[CH3:18].[Cl-].[NH4+]>O1CCCC1>[CH2:15]([O:14][C:12](=[O:13])/[CH:11]=[CH:47]/[C:44]1[CH:45]=[CH:46][C:41]([C@@H:38]2[CH2:39][CH2:40][C@H:36]([N:23]([C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:49])[C@@H:24]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH2:37]2)=[CH:42][CH:43]=1)[CH3:16]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86665256HCID 86665256, compound

Product 1

HCID 67296271HCID 67296271, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen stream, sodium hydride (60% in mineral-oil dispersion) (44 mg, 1.1 mmol) was suspended in tetrahydrofuran (5 mL), followed by addition of ethyl diethylphosphonoacetate (0.24 mL, 1.2 mmol), and the mixture was stirred for 10 minutes at room temperature. A tetrahydrofuran solution of [(1S,3R)-3-(4-formylphenyl)cyclopentyl][(1R)-1-(naphthalen-1-yl)ethyl]carbamic acid tert-butyl ester (407 mg, 0.92 mmol) was added to the mixture, and the mixture was stirred further for 1 hour at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the solution was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (ethyl acetate/hexane: 10/90-15/85) to give the title compound (475 mg).

Workup

  1. stirringthe mixture was stirred further for 1 hour at room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography (ethyl acetate/hexane: 10/90-15/85)

Sources & evidence

ORD record
ord-0e188144259846cd96774925eca81a88
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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