(E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate → Methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)octanoate

HRID 445405노트

반응식

HRID 445405 반응식
[CH:1]1([O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[S:23][CH:22]=[N:21][C:20]=2[CH3:24])[C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([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])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 1

HCID 66822185(E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate

생성물 1

HCID 66822654Methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)octanoate수율 97%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  1. customwas hydrogenated at 1 atm H2 overnight
  2. filtrationThe resulting mixture was then filtered through CELITE
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c64bd30727f94c8b8c646a02007bc082
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476302B2

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