Sulfuric Acid → 9H-Fluoren-9-ylmethyl 12,12-dimethyl-10-oxo-5,8,11-trioxa-2-azatridecanoate

HRID 2275467노트

반응식

HRID 2275467 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:29][C:30](=[CH2:32])[CH3:31].OS(O)(=O)=O>ClCCl>[C:30]([O:27][C:26](=[O:28])[CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])([CH3:32])([CH3:31])[CH3:29]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 27560922-(2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)ethoxy)acetic acid

생성물 1

HCID 675195109H-Fluoren-9-ylmethyl 12,12-dimethyl-10-oxo-5,8,11-trioxa-2-azatridecanoate수율 84.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 150 mg (0.389 mmol) of 8-(9-Fluorenylmethoxycarbonylamino)-3,6-dioxaoctanoic acid, 546 mg (9.73 mmol) isobutylene, and 4.3 μL of 95-98% H2SO4 was stirred at r.t. for 3 days. For workup the reaction solution was diluted with dichloromethane and washed with sat. bicarbonate solution. After drying over sodium sulfate the solvent was removed and the residue obtained purified by chromatography on silica gel with a cHex/EtOAc gradient providing 145 mg (84.4%) of the title compound. ESI MS: 464.12 [M+Na]+.

후처리

  1. washwashed with sat. bicarbonate solution
  2. dry with materialAfter drying over sodium sulfate the solvent
  3. customwas removed
  4. customthe residue obtained
  5. custompurified by chromatography on silica gel with a cHex/EtOAc gradient

출처 및 근거

ORD 기록
ord-d53d78ee4b37400e850abc2db39920ff
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09127044B2

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