3-[1-(5-Ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester → HCID 178436376, compound

HRID 1045052Notes

Reaction equation

HRID 1045052 reaction equation
Br[CH2:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=O.[C:15]([O:19][C:20](=[O:35])[CH2:21][CH2:22][N:23]([CH2:27][C:28]1[S:29][C:30]([CH2:33][CH3:34])=[CH:31][CH:32]=1)[C:24]([NH2:26])=[S:25])([CH3:18])([CH3:17])[CH3:16]>CO>[C:15]([O:19][C:20](=[O:35])[CH2:21][CH2:22][N:23]([C:24]1[S:25][CH:2]=[C:3]([C@H:5]2[CH2:10][CH2:9][C@H:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6]2)[N:26]=1)[CH2:27][C:28]1[S:29][C:30]([CH2:33][CH3:34])=[CH:31][CH:32]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 592267203-[1-(5-Ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl esterHCID 178445648HCID 178445648, compound

Product 1

HCID 178436376HCID 178436376, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromo-1-(trans-4-tert-butyl-cyclohexyl)-ethanone (72 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) to obtain 3-[[4-(trans-4-tert-butyl-cyclohexyl)-thiazol-2-yl]-(5-ethyl-thiophen-2-ylmethyl)-amino]-propionic acid tert-butyl ester (108 mg, 0.220 mmol) following a method analogous to General Procedure C (and similar to the procedure found in Example 5). Hydrolysis of this ester following a method analogous to General Procedure G1 using 1 N NaOH (aq) solution (2 mL), THF (1 mL) and MeOH (1 mL) gave 3-[[4-(trans-4-tert-butyl-cyclohexyl)-thiazol-2-yl]-(5-ethyl-thiophen-2-ylmethyl)-amino]-propionic acid (37 mg, 0.085 mmol). LC-MS m/z: 435 (M+1)+.

Sources & evidence

ORD record
ord-73864e57a6b24af99a75d68be3d0c134
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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