3-[1-(5-Ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester → HCID 178436375, compound
Reaction equation
Br[CH2:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH3:11])[CH2:7][CH2:6]1)=O.[C:12]([O:16][C:17](=[O:32])[CH2:18][CH2:19][N:20]([CH2:24][C:25]1[S:26][C:27]([CH2:30][CH3:31])=[CH:28][CH:29]=1)[C:21]([NH2:23])=[S:22])([CH3:15])([CH3:14])[CH3:13]>CO>[C:12]([O:16][C:17](=[O:32])[CH2:18][CH2:19][N:20]([C:21]1[S:22][CH:2]=[C:3]([C@H:5]2[CH2:10][CH2:9][C@H:8]([CH3:11])[CH2:7][CH2:6]2)[N:23]=1)[CH2:24][C:25]1[S:26][C:27]([CH2:30][CH3:31])=[CH:28][CH:29]=1)([CH3:13])([CH3:14])[CH3:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
2-Bromo-1-(trans-4-methyl-cyclohexyl)-ethanone (61 mg, 0.277 mmol) was added to a methanol (about 4 mL) solution of 3-[1-(5-ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester (100 mg, 0.304 mmol) and the reaction was heated at 60° C. overnight to obtain the 3-[[4-(trans-4-methyl-cyclohexyl)-thiazol-2-yl]-(5-ethyl-thiophen-2-ylmethyl)-amino]-propionic acid tert-butyl ester product following a method analogous to General Procedure C. The solvent was removed at reduced pressure and the residue was dissolved in aqueous saturated sodium bicarbonate solution and ethyl acetate. The aq portion was extracted two times with EtOAc, and the combined organic portion was dried over sodium sulfate. Solvent removal under reduced pressure gave the crude product which was purified by silica gel chromatography (eluent: hexanes→19:1 hexanes:EtOAc→9:1 hexanes:EtOAc) to give the aminothiazole derivative (52 mg).
Sources & evidence
- ORD record
- ord-a6d2d41cc815419fa83308b0293e5c59
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563742B2
Reaction notes
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