Benzyl acetoacetate → (E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

HRID 966533Notes

Reaction equation

HRID 966533 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([I:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:18]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:25]([O:24][C:18](=[O:23])/[CH:19]=[C:20](/[NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])=[CH:10][C:11]=1[I:16])\[CH3:22])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 142266Benzyl acetoacetateHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate

Product 1

HCID 23393855(E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl EsterYield 100.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of (4-amino-3-iodo-benzyl)-carbamic acid tert-butyl ester (3.5 g, 10 mmol) and benzyl acetoacetate (1.92 g, 10 mmol) in benzene (80 mL) was added p-toluenesulfonic acid (95 mg, 0.5 mmol). The mixture was heated at reflux overnight using a Dean Stark condenser. The mixture was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 5.25 g (99%) of crude desired product as a light brown oil: MS(APCI+): m/z 523.1 (MH+). The compound was taken to Step D without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f71db7501cf645a0817b30333b094c68
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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