p-Toluenesulfonic acid monohydrate → HCID 86646165, compound

HRID 551709Notes

Reaction equation

HRID 551709 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:13][CH2:14][C@:15]1([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH2:21][C@@H:20]2[C@H:16]1[CH:17]=[CH:18][CH:19]2[CH2:22][CH3:23]>C1C=CC=CC=1>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[NH2:13][CH2:14][C@:15]1([CH2:24][C:25]([OH:27])=[O:26])[CH2:21][C@@H:20]2[C@H:16]1[CH:17]=[CH:18][CH:19]2[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 90710098HCID 90710098, compound

Product 1

HCID 86646165HCID 86646165, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (2.17 g, 11.4 mmol) was added to a benzene solution (20 mL) of tert-butyl(±) [(1S,5R,6S)-6-(aminomethyl)-2-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (2.75 g, 10.4 mmol), and the mixture was refluxed for 1 hour. The mixture was allowed to cool, and the deposited solid was then washed with methylene chloride to obtain the compound of interest as a gray solid (3.17 g, 80%, Major/Minor=3/1).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureto cool
  3. washthe deposited solid was then washed with methylene chloride
  4. customto obtain the compound of interest as a gray solid (3.17 g, 80%, Major/Minor=3/1)

Sources & evidence

ORD record
ord-e5f51a5706eb4edc80530de672a3fb73
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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