p-Toluenesulfonic acid monohydrate → HCID 86761718, compound

HRID 2190995Notes

Reaction equation

HRID 2190995 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]2[CH:4]1[CH:5]=[C:6]([CH2:10][CH3:11])[CH2:7]2.O.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:21]1([CH3:31])[CH:22]=[CH:23][C:24]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[NH2:1][CH2:2][C@:3]1([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:9][C@@H:8]2[C@H:4]1[CH:5]=[C:6]([CH2:10][CH3:11])[CH2:7]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66803947HCID 66803947, compound

Product 1

HCID 86761718HCID 86761718, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (70 ml, 10.4 v/w) was added to tert-butyl [6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (7.8 g, purity: 86.7%, 22.03 mmol, 87:13 diastereomeric mixture), and the mixture was stirred at room temperature. After addition of p-toluenesulfonic acid monohydrate (4.2 g, 22.03 mmol, 0.87 eq.), the mixture was stirred at room temperature for 3 hours, and a crystal was collected by filtration. Then, the crystal was dried under reduced pressure under the condition of 40° C. to obtain tert-butyl [(1R*,5S*,6S*)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate p-toluenesulfonate as a white crystal (7.8 g, yield: 80.6%, diastereomeric ratio: 99.7:0.3).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. filtrationa crystal was collected by filtration
  3. customThen, the crystal was dried under reduced pressure under the condition of 40° C.

Sources & evidence

ORD record
ord-2ba59e76950949d4b77d57599c833c34
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

Loading…