Hydrochloric Acid → HCID 67918827, compound

HRID 728902Notes

Reaction equation

HRID 728902 reaction equation
[NH2:1]/[C:2](=[CH:8]/[CH:9]([CH3:15])[CH2:10][P:11]([OH:14])([OH:13])=[O:12])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:16][C:17]1[CH:24]=[CH:23]C(CO)=[CH:19][CH:18]=1.Cl>ClCCl>[NH2:1]/[C:2](=[CH:8]/[CH:9]([CH3:15])[CH2:10][P:11]([OH:14])([OH:13])=[O:12])/[C:3]([O:5][CH2:6][C:7]1[CH:23]=[CH:24][C:17]([Cl:16])=[CH:18][CH:19]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 133974-Chlorobenzyl alcoholHCID 86745103HCID 86745103, compound

Product 1

HCID 67918827HCID 67918827, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.37 g (10 mmols) of ethyl E-2-amino-4-methyl-5-phosphono-pentenoate, 14.3 g (100 mmols) of p-chlorobenzyl alcohol, 10 ml of dichloromethane and 20 ml of 4N hydrochloric acid is allowed to stand at room temperature for 1 week. The reaction mixture is evaporated to dryness, the residue is dissolved in 25 ml of ethanol and a solution of 15 ml of propylene oxide in 15 ml of ethanol is added dropwise. The crystalline precipitate formed is collected, washed twice with water, filtrated and dried. p-chlorobenzyl E-2-amino-4-methyl-5-phosphono-pentenoate of m.p. 207°-208° is thus obtained.

Workup

  1. waitto stand at room temperature for 1 week
  2. customThe reaction mixture is evaporated to dryness
  3. dissolutionthe residue is dissolved in 25 ml of ethanol
  4. additiona solution of 15 ml of propylene oxide in 15 ml of ethanol is added dropwise
  5. customThe crystalline precipitate formed
  6. customis collected
  7. washwashed twice with water
  8. filtrationfiltrated
  9. customdried

Sources & evidence

ORD record
ord-2339469dbfb148c28d06805254ee1cb8
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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