Isopropanol → Ethyl 3-phenyl-3-{[3'-(1,3-thiazol-2-ylamino)[1,1'-biphenyl]-3-yl]sulfonylamino}-propanoate

HRID 2229444Notes

Reaction equation

HRID 2229444 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([NH:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:19])=[O:18])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[S:3].Cl[CH:35](OC(Cl)CCl)[CH2:36]Cl.C(O)(C)C>O>[C:28]1([CH:21]([NH:20][S:17]([C:13]2[CH:12]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:2]4[S:3][CH:35]=[CH:36][N:1]=4)[CH:6]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:18])=[O:19])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 149494051,2-Dichloroethyl ether2×HCID 21982442Ethyl 3-[({3'-[(aminocarbothioyl)amino][1,1'-biphenyl]-3-yl}sulfonyl)-amino]-3-phenylpropanoate

Product 1

HCID 21982424Ethyl 3-phenyl-3-{[3'-(1,3-thiazol-2-ylamino)[1,1'-biphenyl]-3-yl]sulfonylamino}-propanoateYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.97 g of Ethyl 3-[({3′-[(aminocarbothioyl)amino][1,1′-biphenyl]-3-yl}sulfonyl)-amino]-3-phenyl-propanoate 14.1.1 and 0.48 g of 1,2-dichloroethylether were heated in water and i-propanol was added such that a clear solution resulted. After 1 h an additional 100 mg of 1,2 dichloroethylether were added and reflux was continued for 1 h. After aqueous work-up and flash chromatography, 0.62 g of the title compound resulted.

Workup

  1. customresulted
  2. temperaturereflux

Sources & evidence

ORD record
ord-09bfff20ff424059b373eb3e3b7650b2
Source dataset
uspto-grants-2002_07
Patent number
US06420396B1

Reaction notes

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