Benzyl Alcohol → dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

HRID 654660Notes

Reaction equation

HRID 654660 reaction equation
[NH2:1][CH:2](/[CH:9]=[C:10](/[CH2:19][P:20]([OH:23])([OH:22])=[O:21])\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]C=1.Cl>C(OCC)C>[NH2:1][CH:2](/[CH:9]=[C:10](/[CH2:19][P:20]([OH:23])([OH:22])=[O:21])\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:10]=[CH:9][CH:2]=[CH:3][CH:4]=1)=[O:5]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 86746004diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

Product 1

HCID 67900429dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3.0 g (9.3 mmol) of diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate in 19.1 ml (185.6 mmol) of benzyl alcohol are added 40 ml of a 4N solution of hydrochloric acid in diethyl ether. The solution formed is allowed to stand for 1 week. The reaction mixture is evaporated to dryness. The residue is dissolved in 35 ml of ethanol, and a solution of 35 ml of propylene oxide in 35 ml of ethanol is added. The crystalline precipitate formed is collected, re-crystallized twice from water and dried over phosphorus pentoxide, affording dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate of m.p. 220°-221° (decomp).

Workup

  1. customThe solution formed
  2. waitto stand for 1 week
  3. customThe reaction mixture is evaporated to dryness
  4. dissolutionThe residue is dissolved in 35 ml of ethanol
  5. additiona solution of 35 ml of propylene oxide in 35 ml of ethanol is added
  6. customThe crystalline precipitate formed
  7. customis collected
  8. customre-crystallized twice from water
  9. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-869afbccc75840f2a17a9c79f79bc1d0
Source dataset
uspto-grants-1992_07
Patent number
US05134134

Reaction notes

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