Ethanol → HCID 54050720, compound

HRID 487488Notes

Reaction equation

HRID 487488 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][C:10]([CH2:21][P:22]([O:28]C(C)C)([O:24]C(C)C)=[O:23])=[CH:11][CH:12]([NH:18]C=O)[C:13]([O:15]CC)=[O:14])=[O:5])[CH3:2].C[Si](C)(C)Br.C(O)C>C(Cl)Cl>[NH2:18][CH:12]([CH:11]=[C:10]([CH2:21][P:22]([OH:28])([OH:24])=[O:23])[CH2:9][CH2:8][O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 86747670HCID 86747670, compound

Product 1

HCID 54050720HCID 54050720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.5 g (11.8 mmol) of ethyl 6-ethoxycarbonylmethoxy-2-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate are dissolved in 55 ml of CH2Cl2 and 6.1 ml (42.3 mmol) of trimethylbromosilane are then 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 55 ml of ethanol, allowed to stand for a further 24 hours. The reaction mixture is concentrated by evaporation, the residue is dissolved in 24 ml of ethanol, and a mixture of 55 ml of propylene oxide and 55 of ethanol is added dropwise to this solution. The suspension so obtained is stirred for 1 hour and then filtered with suction. The filter product is dried giving 2-amino-6-ethoxycarbonylmethoxy-4-phosphonomethyl-hex-3-enoic acid with a melting point of 213°-215° C. (decomp.) as a white oil.

Workup

  1. waitto stand for a further 24 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. dissolutionthe residue is dissolved in 24 ml of ethanol
  4. additiona mixture of 55 ml of propylene oxide and 55 of ethanol
  5. additionis 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-42ec3cf924004ef28c55259eb4453e0a
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

Loading…