Ammonium Chloride → 2-tert-Butoxycarbonylamino-3-fluorobenzoic acid 2-hydroxyethyl ester

HRID 558980노트

반응식

HRID 558980 반응식
[Si]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:28])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1>[OH:8][CH2:9][CH2:10][O:11][C:12](=[O:28])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 669995852-tert-Butoxycarbonylamino-3-fluorobenzoic acid 2-(tert-butyldimethylsilanyloxy)ethyl ester

생성물 1

HCID 669999872-tert-Butoxycarbonylamino-3-fluorobenzoic acid 2-hydroxyethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-tert-butoxycarbonylamino-3-fluorobenzoic acid 2-(tert-butyldimethylsilanyloxy)ethyl ester from Example 19B (1.2 g, 2.9 mmol) in THF (25 ml) was added a solution tetrabutylammonium fluoride (1.0M, 5.8 ml, 5.8 mmol) in THF while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 18 h. Saturated ammonium chloride solution (20 ml) was added and the mixture was stirred for 1 h and evaporated in vacuo. The residue was partitioned between chloroform and water and the organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 90:10) to give a colourless gum; yield 180 mg, 21%.

후처리

  1. temperaturewhile cooling in an ice/water bath
  2. stirringthe mixture was stirred for 1 h
  3. customevaporated in vacuo
  4. customThe residue was partitioned between chloroform and water
  5. customthe organic phase was dried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 90:10)
  8. customto give a colourless gum

출처 및 근거

ORD 기록
ord-7723bc37ca0c4228b3bb6b5803c3c8c2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063038B2

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