Toluene → Ethyl 2-{[(benzyloxy)carbonyl]amino}prop-2-enoate

HRID 546269Notes

Reaction equation

HRID 546269 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=O.C([NH:16][C:17]([O:19]CC)=[O:18])C1C=CC=CC=1.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.O>[CH2:28]([O:19][C:17]([NH:16][C:2](=[CH2:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 12041Ethyl pyruvateHCID 75801Ethyl benzylcarbamate

Product 1

HCID 14334458Ethyl 2-{[(benzyloxy)carbonyl]amino}prop-2-enoate

Reagents, catalysts & solvents 3

HCID 785HydroquinoneCatalystHCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

288 g of ethyl pyruvate, 250 g of benzylurethane, 2.5 g of p-toluenesulphonic acid and 1 g of hydroquinone are introduced into 2.5 l of toluene and refluxed for 9 h in a water separator. The reaction solution is then filtered through silica gel and washed with 500 ml of toluene. The filtrate is treated with 1 g of hydroquinone and concentrated to the greatest possible extent on a rotary evaporator. 376 g of ethyl N-benzyloxycarbonyl-2-amino-acrylate are obtained as an oil, which according to HPLC has a purity of about 90%.

Workup

  1. filtrationThe reaction solution is then filtered through silica gel
  2. washwashed with 500 ml of toluene
  3. additionThe filtrate is treated with 1 g of hydroquinone
  4. concentrationconcentrated to the greatest possible extent on a rotary evaporator

Sources & evidence

ORD record
ord-ae5111b78cfd440a82291d4ad25403af
Source dataset
uspto-grants-2011_05
Patent number
US07935831B2

Reaction notes

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