Ethanol → HCID 53809512, compound

HRID 376150Notes

Reaction equation

HRID 376150 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]([CH2:22][P:23]([O:29]C(C)C)([O:25]C(C)C)=[O:24])=[CH:12][CH:13]([NH:19]C=O)[C:14]([O:16]CC)=[O:15])=[O:5])[CH3:2].C[Si](C)(C)Br.C(O)C>C(Cl)Cl>[NH2:19][CH:13]([CH:12]=[C:11]([CH2:22][P:23]([OH:29])([OH:25])=[O:24])[CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 54415170HCID 54415170, compound

Product 1

HCID 53809512HCID 53809512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.4 g (5 mmol) of ethyl 7-ethoxycarbonylmethoxy-2-formylamino-4-diisopropylphosphonomethyl-hept-3-enoate are dissolved in 24 ml of CH2Cl2. Then 2.6 ml (20 mmol) of trimethylbromosilane are added dropwise at room temperature to this solution. The reaction mixture is allowed to stand for 24 hours at room temperature and, after the dropwise addition of 24 ml of ethanol, allowed to stand again for 24 hours. The reaction mixture is concentrated by evaporation and the residue is dissolved in 24 ml of ethanol. A mixture of 24 ml of propylene oxide and 24 ml of ethanol is then added dropwise to this solution. The suspension so obtained is stirred for 1 hour at 0° C. and then filtered with suction. The filter product is dried, giving 2-amino-7-ethoxycarbonylmethoxy-4-phosphonomethyl-hept-3-enoic acid with a melting point of 215°-218° C.

Workup

  1. waitto stand again for 24 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. dissolutionthe residue is dissolved in 24 ml of ethanol
  4. additionA mixture of 24 ml of propylene oxide and 24 ml of ethanol
  5. additionis then added dropwise to this solution
  6. customThe suspension so obtained
  7. filtrationfiltered with suction
  8. customThe filter product is dried

Sources & evidence

ORD record
ord-6ee885cf1d7d4fa39ff63ecd2ec7087c
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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