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

HRID 1925202Notes

Reaction equation

HRID 1925202 reaction equation
[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]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 27560921-(9H-Fluoren-9-yl)-3-oxo-2,7,10-trioxa-4-azadodecan-12-oic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-cc6a8fc870d34708afb2a165b16876d5
Source dataset
uspto-grants-2012_05
Patent number
US08178650B2

Reaction notes

Loading…