Ethanol → HCID 53933743, compound

HRID 376129Notes

Reaction equation

HRID 376129 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([NH:26]C=O)[CH:6]=[C:7]([CH2:15][P:16]([O:22]C(C)C)([O:18]C(C)C)=[O:17])[CH2:8][CH2:9][N:10]([C:12](=[O:14])[CH3:13])[CH3:11])[CH3:2].C[Si](C)(C)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([NH2:26])[CH:6]=[C:7]([CH2:15][P:16]([OH:22])([OH:18])=[O:17])[CH2:8][CH2:9][N:10]([C:12](=[O:14])[CH3:13])[CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 53756131HCID 53756131, compound

Product 1

HCID 53933743HCID 53933743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.2 g (18.9 mmol) of 6-(N-acetyl-N-methylamino)-4-diisopropylphosphonomethyl-2-formylamino-hex-3-enoic acid ethyl ester are dissolved in 40 ml of dichloromethane, and 9.8 ml (75.6 mmol) of trimethylbromosilane are added dropwise at room temperature. The mixture is left to stand at room temperature for 24 hours, 40 ml of ethanol are added dropwise, the mixture is left to stand for a further 24 hours and is concentrated by evaporation, the residue is dissolved in 40 ml of ethanol, and a mixture of 40 ml of propylene oxide and 40 ml of ethanol is added dropwise. A suspension forms, which is stirred for a further one hour at room temperature and for one hour at 0° and is then filtered with suction. Drying yields 6-(N-acetyl-N-methylamino)-2-amino-4-phosphonomethyl-hex-3-enoic acid ethyl ester having a melting point of 222°-223° C. (decomp.).

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. waitto stand for a further 24 hours
  4. concentrationis concentrated by evaporation
  5. dissolutionthe residue is dissolved in 40 ml of ethanol
  6. additiona mixture of 40 ml of propylene oxide and 40 ml of ethanol
  7. additionis added dropwise
  8. filtrationis then filtered with suction
  9. customDrying

Sources & evidence

ORD record
ord-fcbe87dfe540456eb656db4452a65cbf
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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