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Hydrochloric Acid → [2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclopentyl-acetic acid

HRID 417152
ノート
印刷プレビュー

反応式

HRID 417152 の反応式
C(N(N=O)[C:9](=[O:34])[CH:10]([N:16]1[C:20]2[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:19]=2[N:18]=[C:17]1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1.[OH2:37].[OH-].[Li+].OO.Cl>O1CCCC1.O.C(OCC)(=O)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:17]2[N:16]([CH:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]([OH:37])=[O:34])[C:20]3[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:19]=3[N:18]=2)=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 86639902N-benzyl-N-nitroso-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopentyl-acetamide

生成物 1

HCID 66619513[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclopentyl-acetic acid

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
3 回
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a ice-cold suspension of 8.10 g (15.91 mmol) N-benzyl-N-nitroso-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopentyl-acetamide in 45 ml tetrahydrofuran and ml water were added dropwise over 30 min. a solution of 6.68 g (159 mmol) lithium hydroxide monohydrate in 32.50 ml (318 mmol) 30% hydrogen peroxide solution and 15 ml water. After stirring for 4.5 h at room temperature, 150 ml water and 100 ml ethyl acetate were added and the pH adjusted to 1 using 25% aqueous hydrochloric acid. The phases were separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, then dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate:methanole (100:0:0 to 0:100:0 to 0:85:15). Off-white solid (55%). MS (Turbo Spray): m/z=391.1 [M+H].

後処理

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of heptane

出典と根拠

ORDレコード
ord-1bf725b02daf474ca101f50e46cbcdeb
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08088930B2

反応ノート

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