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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
ノート
印刷プレビュー

反応式

HRID 220695 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180
Acetone
溶媒
HCID 962Water溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-e5e48a23d1514856986822e3fe223cc6
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202895B2

反応ノート

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