Cyclohexane → p-Methoxybenzyl alpha-amino-dimethylphosphonoacetate

HRID 1658028Notes

Reaction equation

HRID 1658028 reaction equation
C(=[N:8][CH:9]([P:22]([O:26][CH3:27])([O:24][CH3:25])=[O:23])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:11])C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1>CCOCC>[NH2:8][CH:9]([P:22]([O:26][CH3:27])([O:24][CH3:25])=[O:23])[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)=[O:11]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 54064440p-methoxybenzyl N-benzylidene-alpha-amino-dimethylphosphonoacetate

Product 1

HCID 21529965p-Methoxybenzyl alpha-amino-dimethylphosphonoacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

p-Methoxybenzyl N-benzylidene-α-amino-dimethylphosphonoacetate (9.78 g) in ether (50 ml) is added over 20 minutes to a stirring solution of p-toluenesulfonic acid monohydrate (4.76 g) in ether (150 ml). Cyclohexane (100 ml) is added and the solvents are decanted off. The residue is washed with more 2:1 ether-cyclohexane, which is again decanted off. The residue is partitioned between methylene chloride and 1 M dipotassium hydrogen phosphate (50 ml). The organic portion is separated, washed with water, dried, and evaporated in vacuo to give p-methoxybenzyl α-aminodimethylphosphonoacetate.

Workup

  1. customthe solvents are decanted off
  2. washThe residue is washed with more 2:1 ether-cyclohexane, which
  3. customis again decanted off
  4. customThe residue is partitioned between methylene chloride and 1 M dipotassium hydrogen phosphate (50 ml)
  5. customThe organic portion is separated
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-68f825aa3f964ab7a444afb4f4d7046b
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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