Ethanol → HCID 53769333, compound

HRID 376099Notes

Reaction equation

HRID 376099 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH:25]C=O)[CH:6]=[C:7]([CH2:14][P:15]([O:21]C(C)C)([O:17]C(C)C)=[O:16])[CH2:8][CH2:9][O:10]C(=O)C)[CH3:2].C[Si](C)(C)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH2:25])[CH:6]=[C:7]([CH2:14][P:15]([OH:17])([OH:21])=[O:16])[CH2:8][CH2:9][OH:10])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 54076214HCID 54076214, compound

Product 1

HCID 53769333HCID 53769333, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.57 g (8.5 mmol) of 6-acetoxy-4-diisopropylphosphonomethyl-2-formylamino-hex-3-enoic acid ethyl ester are dissolved in 22 ml of dichloromethane, and 4.4 ml (34 mmol) of trimethylbromosilane are added dropwise at room temperature. The mixture is left to stand at room temperature for 22 hours, 22 ml of ethanol are added dropwise, the mixture is left to stand for a further 22 hours and is concentrated by evaporation in a rotary evaporator, the residue is dissolved in 22 ml of ethanol, and a mixture of 22 ml of propylene oxide and 22 ml of ethanol is added dropwise. A suspension forms, which is stirred for a further 90 minutes and then filtered with suction. 2-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoic acid ethyl ester having a melting point of 195° (decomp.) is obtained.

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. waitto stand for a further 22 hours
  4. concentrationis concentrated by evaporation in a rotary evaporator
  5. dissolutionthe residue is dissolved in 22 ml of ethanol
  6. additiona mixture of 22 ml of propylene oxide and 22 ml of ethanol
  7. additionis added dropwise
  8. filtrationfiltered with suction

Sources & evidence

ORD record
ord-17ad7aa9f1924c12b369eaae344b2344
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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