p-Toluenesulfonic acid → Methyl 2-hydroxy-8-(4-methylthiazol-5-yl)octanoate

HRID 445406Notes

Reaction equation

HRID 445406 reaction equation
C1([O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[S:23][CH:22]=[N:21][C:20]=2[CH3:24])[C:9]([O:11][CH3:12])=[O:10])CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[S:23][CH:22]=[N:21][C:20]=1[CH3:24])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66822654Methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)octanoate

Product 1

HCID 66821983Methyl 2-hydroxy-8-(4-methylthiazol-5-yl)octanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate (560 mg, 1.58 mmol) and ethanol (40 mL) was added 10% palladium on carbon (82 mg) and the resulting mixture was hydrogenated at 1 atm H2 overnight. The resulting mixture was then filtered through CELITE and concentrated in vacuo to yield methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)octanoate (97%) which was used in the next step without further purification. A solution of methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)octanoate (563 mg, 1.58 mmol), methanol (8.6 mL), and p-toluenesulfonic acid (14.8 mg, 0.086 mmol) was stirred at room temperature for 1 h. Solvent was removed in vacuo to yield methyl 2-hydroxy-8-(4-methylthiazol-5-yl)octanoate which was used in the next step without further purification. A mixture of 2-hydroxy-8-(4-methylthiazol-5-yl)octanoic acid (590 mg, 2.17 mmol), tetrahydrofuran (21 mL), water (54 mL) and lithium hydroxide (78.1 mg, 3.26 mmol) was stirred at room temperature for 2 h. The resulting mixture was acidified with 1N HCl and concentrated in vacuo. An excess amount of acetonitrile was added to the residue and the mixture was concentrated. The process was repeated twice to yield 2-hydroxy-8-(4-methylthiazol-5-yl)octanoic acid which was used in the next step without further purification. MS (ES+) 258 (M+1).

Workup

  1. customwas used in the next step without further purification
  2. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-7384d8bef4d746b1ae1182a2f2ccc88a
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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