Hydrochloric Acid → Ethyl [4-(1-hydroxy-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate

HRID 460028노트

반응식

HRID 460028 반응식
[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:33])[CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[BH4-].[Na+].Cl.O>C(O)C>[OH:33][CH:15]([C:13]1[CH:12]=[CH:11][C:3]([O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]([CH3:1])[CH:14]=1)[CH2:16][C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH3:32]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 58824797Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

생성물 1

HCID 17972190Ethyl [4-(1-hydroxy-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate (intermediated 15, 0.165 g) in absolute ethanol (5 ml) at 0° C. under nitrogen was added sodium borohydride (0.013 g) after stirring for an hour the reaction was allowed to come to room temperature and stirred for a further two hours. 2M aqueous hydrochloric acid was then added drop-wise and once the effervescence had subsided water was added, the product was extracted twice with ethyl acetate and the combined organic extracts were dried (magnesium sulfate) filtered and evaporated. The product was purified by flash column chromatography using cyclohexane then ethyl acetate:cyclohexane(1:4) as eluents to give title compound as a pale yellow solid.

후처리

  1. customto come to room temperature
  2. stirringstirred for a further two hours
  3. additionwas added
  4. extractionthe product was extracted twice with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-f0d53c3dc6574ac88e3af61cf76c320c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196107B2

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