Water → 2-Naphthalen-1-yl-5-phenyl-1-(2-trimethylsilanyl-ethoxycarbonylamino)-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1265280Notes

Reaction equation

HRID 1265280 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([C:15]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=O)[CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[CH3:28][Si:29]([CH3:38])([CH3:37])[CH2:30][CH2:31][O:32][C:33]([NH:35][NH2:36])=[O:34].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:36]([NH:35][C:33]([O:32][CH2:31][CH2:30][Si:29]([CH3:38])([CH3:37])[CH3:28])=[O:34])[C:15]=1[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[O:27])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 10241327Hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl esterHCID 205827512-(Naphthalene-1-carbonyl)4-oxo-4-phenyl-butyric acid ethyl ester

Product 1

HCID 205827492-Naphthalen-1-yl-5-phenyl-1-(2-trimethylsilanyl-ethoxycarbonylamino)-1H-pyrrole-3-carboxylic acid ethyl esterYield 95.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-(Naphthalene-1-carbonyl)-4-oxo-4-phenyl-butyric acid ethyl ester (1 g, 2.77 mmol) in toluene (6.5 mL) was treated with Hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl ester (599 mg, 3.34 mmol) and p-toluene sulfonic acid (33 mg). The resulting solution was heated to reflux, with the azeotropic removal of water (Dean Stark trap), under Ar for 6 h, cooled to rt and concentrated in vacuo to afford 2-Naphthalen-1-yl-5-phenyl-1-(2-trimethylsilanyl-ethoxycarbonylamino)-1H-pyrrole-3-carboxylic acid ethyl ester (1.33 g), which was not purified, but used immediately in the next reaction.

Workup

  1. temperatureThe resulting solution was heated
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-440a9d322b4a4962a2a9f15e7e05f866
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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