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

HRID 445406ノート

反応式

HRID 445406 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7384d8bef4d746b1ae1182a2f2ccc88a
出典データセット
uspto-grants-2013_07
特許番号
US08476302B2

反応ノート

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