p-Toluenesulfonic acid monohydrate → HCID 86646147, compound

HRID 551681Notes

Reaction equation

HRID 551681 reaction equation
C(OC([NH:8][CH2:9][C@@:10]1([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH2:16][C@H:15]2[C@@H:11]1[C:12]([CH3:18])=[C:13]([CH3:17])[CH2:14]2)=O)(C)(C)C.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.C1(SC)C=CC=CC=1>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[NH2:8][CH2:9][C@@:10]1([CH2:19][C:20]([OH:22])=[O:21])[CH2:16][C@H:15]2[C@@H:11]1[C:12]([CH3:18])=[C:13]([CH3:17])[CH2:14]2

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131728920HCID 131728920, compound

Product 1

HCID 86646147HCID 86646147, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7520ThioanisoleSolvent

Procedure

Tert-butyl(±)-[(1S,5R,6R)-6-(tert-butoxycarbonylamino)methyl-3,4-dimethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (4.0 g, 11 mmol) and p-toluenesulfonic acid monohydrate (2.5 g, 13 mmol) were suspended in toluene (30 mL) and thioanisole (3.8 mL), and the suspension was stirred at 80° C. for 2 hours. The reaction solution was concentrated, and the resulting oil substance was treated with ethyl acetate and hexane to obtain the title compound (2.3 g, 55%) as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe resulting oil substance was treated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-35fcb333fd6845dca2dbae7bfdc66d17
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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