2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → 1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole
Reaction equation
Cl[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:6]=1)=O.[C:23]([C:27]([O:29][CH2:30][C:31]([NH2:33])=[S:32])=[O:28])([CH3:26])([CH3:25])[CH3:24]>C(O)C>[CH:17]1([CH2:16][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][C:9]=3[O:14][CH3:15])[C:5]([C:3]3[N:33]=[C:31]([CH2:30][O:29][C:27]([C:23]([CH3:26])([CH3:24])[CH3:25])=[O:28])[S:32][CH:2]=3)=[CH:6]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Chloro-1-[1-(cyclohexyl)methyl-7-methoxy-1H-indol-3-yl]ethanone (0.73 g, 2.30 mmol) and 2-(tert-butylcarbonyloxy)thioacetamide (1.21 g, 6.89 mmol) were suspended in ethanol (10 ml) and the resulting mixture subjected to microwave irradiation at 150° C. for 10 min using an Emrys™ Optimizer EXP. The reaction mixture was concentrated in vacuo and the residue obtained was purified by flash column chromatography eluting with 5% (v/v) ethyl acetate in n-heptane to afford 1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole as a yellow oil (1.01 g).
Workup
- customirradiation at 150° C. for 10 min
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue obtained
- customwas purified by flash column chromatography
- washeluting with 5% (v/v) ethyl acetate in n-heptane
Sources & evidence
- ORD record
- ord-c3f0251913df425da83855f20c89a5c2
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700634B2
Reaction notes
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