Methylparaben → 4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylethoxy]-benzoic acid methyl ester

HRID 253206

반응식

HRID 253206 반응식
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:7][C:8]=1[CH3:9].[CH3:20][O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:20][O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([O:1][CH2:2][CH2:3][C:4]2[N:5]=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[S:7][C:8]=2[CH3:9])=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 226474902-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

생성물 1

HCID 579867424-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylethoxy]-benzoic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(2-hydroxy-ethyl)-5-methyl-2-(4-trifluoromethyl-phenyl)thiazole (Example 3, 288 mg, 1.0 mmol) in THF (3 mL) add 4-hydroxy-benzoic acid methyl ester (167 mg, 1.1 mmol) followed by triphenylphosphine (288 mg, 1.1 mmol). To this solution, add, dropwise, diethyl azodicarboxylate (174 μL, 1.1 mmol). On complete addition, stir the resulting red solution for 20 min. concentrate under reduced pressure and purify the residue by flash chromatography (elute with 15% ethyl acetate/15% dichloromethane in heptane) to give the title compound as a white solid. (410 mg).

후처리

  1. additionTo this solution, add
  2. additionOn complete addition
  3. concentrationconcentrate under reduced pressure
  4. custompurify the residue
  5. washby flash chromatography (elute with 15% ethyl acetate/15% dichloromethane in heptane)

출처 및 근거

ORD 기록
ord-94a4d05db2fd43ba88eddf76f596e435
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872032B2

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