9-Fluorenylmethyl chloroformate → HCID 67460372, compound

HRID 554005Notes

Reaction equation

HRID 554005 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[OH:19][CH2:20][CH:21]1[NH:26][CH:25]([C:27]2[CH:32]=[C:31]([F:33])[C:30]([F:34])=[C:29]([F:35])[CH:28]=2)[CH2:24][N:23]([C:36]([O:38][CH3:39])=[O:37])[CH2:22]1>C(Cl)Cl.O.C(=O)(O)[O-].[Na+]>[CH3:39][O:38][C:36]([N:23]1[CH2:24][CH:25]([C:27]2[CH:28]=[C:29]([F:35])[C:30]([F:34])=[C:31]([F:33])[CH:32]=2)[N:26]([C:2]([O:4][CH2:5][CH:6]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:3])[CH:21]([CH2:20][OH:19])[CH2:22]1)=[O:37]

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 67465999HCID 67465999, compound

Product 1

HCID 67460372HCID 67460372, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86585896Sodium bicarbonate waterSolvent

Procedure

9-Fluorenylmethyl chloroformate (958 mg) was added to a mixed solution of methyl 3-hydroxymethyl-5-(3,4,5-trifluorophenyl)piperazine-1-carboxylate (867 mg) in methylene chloride (20 mL) and saturated sodium bicarbonate water (20 mL), and the reaction solution was stirred at room temperature for 14 hours. The organic layer was separated from the reaction solution. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane->ethyl acetate) to obtain 916 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customThe organic layer was separated from the reaction solution
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane->ethyl acetate)

Sources & evidence

ORD record
ord-b21b95b4e9434851944d31478ccd8f61
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

Loading…