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

HRID 2275467ノート

反応式

HRID 2275467 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-d53d78ee4b37400e850abc2db39920ff
出典データセット
uspto-grants-2015_09
特許番号
US09127044B2

反応ノート

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