Tetrahydrofuran → HCID 178436374, compound

HRID 1045053Notes

Reaction equation

HRID 1045053 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][CH2:8][N:9]([C:18]1[S:19][CH:20]=[C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25][CH2:24]2)[N:22]=1)[CH2:10][C:11]1[S:12][C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=1)(C)(C)C.[OH-].[Na+].C1COCC1>CO>[C:29]([C@H:26]1[CH2:27][CH2:28][C@H:23]([C:21]2[N:22]=[C:18]([N:9]([CH2:10][C:11]3[S:12][C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=3)[CH2:8][CH2:7][C:6]([OH:33])=[O:5])[S:19][CH:20]=2)[CH2:24][CH2:25]1)([CH3:31])([CH3:32])[CH3:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178436376HCID 178436376, compound

Product 1

HCID 178436374HCID 178436374, compound

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-baa6954ef52f41e3a03b16b1a44ddbe8
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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