Trimethyl phosphonoacetate → HCID 67043500, compound

HRID 539625Notes

Reaction equation

HRID 539625 reaction equation
[Li+].[Cl-].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[CH2:14]([O:21][C:22](=[O:35])[NH:23][CH:24]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:25]CC=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C.C(OCC)C.[NH4+].[Cl-]>[CH3:3][O:4][C:5](=[O:6])[CH2:7][CH2:25][CH:24]([NH:23][C:22]([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 433294Lithium ChlorideHCID 58200258HCID 58200258, compound

Product 1

HCID 67043500HCID 67043500, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a stirring room temperature suspension of LiCl (0.84 g, 19.8 mmol) in dry acetonitrile (50 mL) was added trimethyl phosphonoacetate (4 mL, 24.75 mmol). The resulting mixture was stirred for 5 minutes, then TEA (2.76 mL, 19.8 mmol) was added. The reaction mixture was stirred for 10 minutes, and then a solution of (4-oxo-1-phenyl-butyl)-carbamic acid benzyl ester (16.5 mmol) in acetonitrile (15 mL) was added. The reaction mixture was stirred at room temperature for 18 hours, then diluted with diethyl ether and saturated aqueous NH4Cl. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to an oil, which was chromatographed (5%-40% EtOAc in hexanes) to give 4.41 g (79%) of 4-benzyloxycarbonylamino-4-phenyl-butyric acid methyl ester as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 10 minutes
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil, which
  8. customwas chromatographed (5%-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbe3557726e34e04859247f4486392e3
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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