Ethanol → diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

HRID 654654Notes

Reaction equation

HRID 654654 reaction equation
C([NH:3][CH:4](/[CH:11]=[C:12](/[CH2:21][P:22]([O:28]C(C)C)([O:24]C(C)C)=[O:23])\[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.C[Si](C)(C)Br.C(O)C>ClCCl>[NH2:3][CH:4](/[CH:11]=[C:12](/[CH2:21][P:22]([OH:28])([OH:24])=[O:23])\[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 86746005diethyl E-2-formylamino-4-diisopropylphosphonomethyl-hept-3-ene-1,7-dicarboxylate

Product 1

HCID 86746004diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.3 g (9.9 mmol) of diethyl E-2-formylamino-4-diisopropylphosphonomethyl-hept-3-ene-1,7-dicarboxylate are dissolved in 14 ml of dichloromethane and 5.2 ml (40 mmol) of trimethylbromosilane are added dropwise at room temperature to the solution. The reaction mixture is allowed to stand for 20 hours and, after addition of 14 ml of ethanol, allowed to stand for a further 19 hours. The reaction mixture is concentrated on a rotary evaporator and the residue is taken up in 14 ml of ethanol. After addition of 14 ml of propylene oxide and 14 ml of ethanol, the resultant suspension is stirred for 90 minutes and then filtered with suction, affording diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7 -dicarboxylate of m.p. 218°-220° C. (decomp.).

Workup

  1. waitto stand for a further 19 hours
  2. concentrationThe reaction mixture is concentrated on a rotary evaporator
  3. additionAfter addition of 14 ml of propylene oxide and 14 ml of ethanol
  4. filtrationfiltered with suction

Sources & evidence

ORD record
ord-dbdde1c99f71471cad1ae13bc0d92fcc
Source dataset
uspto-grants-1992_07
Patent number
US05134134

Reaction notes

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