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Hydrochloric Acid → 1-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane

HRID 2309600
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HRID 2309600 반응식
[C:1]1(=[O:39])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:10][C:11]([F:23])([F:22])[CH2:12][CH2:13][O:14]CC2C=CC=CC=2)[C:4](=[O:34])[C:3]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:2]12.C[Si](I)(C)C.C(N(CC)CC)C.Cl>ClCCl.CO>[C:4]1(=[O:34])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[CH2:10][C:11]([F:23])([F:22])[CH2:12][CH2:13][OH:14])[C:1](=[O:39])[C:2]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:3]12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 198607071-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane

생성물 1

HCID 198606861-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane

시약·촉매·용매 2

HCID 887
Methanol
용매
2회
HCID 6344Dichloromethane용매2회

실험 절차

A solution of 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane (9.5 g, 17.1 mM) and trimethylsilyl iodide (2.7 mL, 10% excess) in dry dichloromethane is stirred overnight at room temperature under nitrogen. Triethylamine (3 g) is added, and stirring is continued for 1 hour at room temperature. Following the addition of more dichloromethane, the reaction mixture is washed with 1N HCl (twice), aqueous NaHSO3 (twice), brine (twice), and dried (Na2SO4). The solvents are removed by evaporation to yield an oil. This oil is dissolved in methanol and 1 mL of a 9N solution of HCl in methanol is added. The mixture is evaporated and stripped twice with CCl4 to provide an oil, which upon scratching with ether/petroleum ether yields 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane as slightly violet crystals: 6.8 g (85%).

후처리

  1. washthe reaction mixture is washed with 1N HCl (twice), aqueous NaHSO3 (twice), brine (twice), and
  2. dry with materialdried (Na2SO4)
  3. customThe solvents are removed by evaporation
  4. customto yield an oil
  5. customThe mixture is evaporated
  6. customto provide an oil, which

출처 및 근거

ORD 기록
ord-d3425e8bf6bc4d3482445f838d219460
출처 데이터셋
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04695654

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