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Hydrochloric Acid → [4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetic acid

HRID 220695
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HRID 220695 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:18])[N:11]([CH2:13][C:14]([O:16]C)=[O:15])[CH:12]=2)=[CH:4][CH:3]=1.Br[CH2:20][CH:21]([OH:26])[C:22]([F:25])([F:24])[F:23].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][CH:21]([OH:26])[C:22]([F:25])([F:24])[F:23])[C:10](=[O:18])[N:11]([CH2:13][C:14]([OH:16])=[O:15])[CH:12]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 58012289Methyl[4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

생성물 1

HCID 59536810[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetic acid

시약·촉매·용매 2

HCID 180
Acetone
용매
HCID 962Water용매

실험 절차

A quantity of 1.0 g (3.75 mmol) of methyl [4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]acetate (prepared according to WO 2007/134862 Example 323A) was dissolved with 796 mg (4.13 mmol) of 3-bromo-1,1,1-trifluoropropan-2-ol in 50 ml of acetone, 1.47 g (4.50 mmol) of caesium carbonate were added at RT, and the mixture was heated under reflux for 16 h. For work-up, it was cooled to RT and admixed with 50 ml of water. It was neutralised by addition of 1M hydrochloric acid and extracted with three times 50 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC [Method 19]. This gave 171 mg (13% of theory) of the target compound.

후처리

  1. additionwere added at RT
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 h
  4. extractionextracted with three times 50 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by preparative HPLC [Method 19]

출처 및 근거

ORD 기록
ord-e5e48a23d1514856986822e3fe223cc6
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202895B2

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