Ethanol → HCID 53676203, compound

HRID 376116Notes

Reaction equation

HRID 376116 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([NH:22]C=O)[CH:6]=[C:7]([CH2:11][P:12]([O:18]C(C)C)([O:14]C(C)C)=[O:13])[CH2:8][CH2:9][F:10])[CH3:2].C[Si](C)(C)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([NH2:22])[CH:6]=[C:7]([CH2:11][P:12]([OH:14])([OH:18])=[O:13])[CH2:8][CH2:9][F:10])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 53931620HCID 53931620, compound

Product 1

HCID 53676203HCID 53676203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.52 g (1.36 mmol) of 4-diisopropylphosphonomethyl-6-fluoro-2-formylamino-hex-3-enoic acid ethyl ester is dissolved in 3.5 ml of dichloromethane, and 0.7 ml (5.45 mmol) of trimethylbromosilane is added dropwise at room temperature. The mixture is left to stand at room temperature for 24 hours, 3.5 ml of ethanol are added dropwise, the mixture is left to stand for a further 24 hours and is concentrated by evaporation in a rotary evaporator, the residue is dissolved in 2.4 ml of ethanol, and a mixture of 0.6 ml of propylene oxide and 0.6 ml of ethanol is added. A suspension forms, which is stirred for a further 2 hours at room temperature and for 2 hours with ice cooling and is then filtered with suction. 2-amino-6-fluoro-4-phosphonomethyl-hex-3-enoic acid ethyl ester having a melting point of 222° (decomp.) is obtained.

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. waitto stand for a further 24 hours
  4. concentrationis concentrated by evaporation in a rotary evaporator
  5. dissolutionthe residue is dissolved in 2.4 ml of ethanol
  6. additiona mixture of 0.6 ml of propylene oxide and 0.6 ml of ethanol
  7. additionis added
  8. filtrationis then filtered with suction

Sources & evidence

ORD record
ord-c48ff9bcf171429091e07d44b6a71078
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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