HCID 21584574, compound → HCID 67524566, compound

HRID 898854Notes

Reaction equation

HRID 898854 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([NH:18][S:19]([N:22]2[CH2:26]COC2=O)(=[O:21])=[O:20])[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:9]1[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([CH:32]1[CH2:37]NC[CH2:34][N:33]1[C:38]([OH:40])=[O:39])(C)(C)C>>[C:1]([O:40][C:38]([N:33]1[CH2:32][CH2:37][N:22]([S:19](=[O:20])(=[O:21])[NH:18][C@:8]2([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C@@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:9]2[CH3:17])[CH2:26][CH2:34]1)=[O:39])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21584574HCID 21584574, compoundHCID 67526208HCID 67526208, compound

Product 1

HCID 67524566HCID 67524566, compoundYield 158.8%

Procedure

Under argon atmosphere, this (1S,2R,3R)-2-methyl-1-(2-oxo-oxazolidine-3-sulfonylamino)-3-phenyl-cyclopropanecarboxylic acid t-butyl ester (0.61 mmol) and t-butyl-1-piperazinecarboxylic acid (0.14 g, 0.73 mmol) were mixed, and the mixture was refluxed for 18 hours under heating. The obtained solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:0 to 5:1) to give the title compound (0.24 g, yield 79%).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureunder heating
  3. concentrationThe obtained solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:0 to 5:1)

Sources & evidence

ORD record
ord-935454b59b7e47f8a672eab3c77c3cbe
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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