p-Toluenesulfonic acid monohydrate → HCID 12162546, compound

HRID 1776210Notes

Reaction equation

HRID 1776210 reaction equation
[N:1]12[CH2:6][CH:5]1[CH2:4][CH2:3][S:2]2(=[O:8])=[O:7].[OH2:9].[C:10]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:10][O:9][CH:5]1[CH2:4][CH2:3][S:2](=[O:8])(=[O:7])[NH:1][CH2:6]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11320954HCID 11320954, compound

Product 1

HCID 12162546HCID 12162546, compoundYield 677.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-thia-1-azabicyclo[3.1.0]hexane 2,2-dioxide (0.600 g, 4.5 mmol), p-toluenesulfonic acid hydrate (0.086 g, 0.5 mmol) and methanol (50 mL) was stirred at room temperature for 3 days. The reaction was concentrated and the residue purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the product as a white solid (0.56 g, 75%). 1H NMR (300 MHz, CDCl3) δ 4.43 (br s, 1H), 3.65-3.40 (m, 2H), 3.40 (s, 3H), 3.36-3.23 (m, 2H), 3.08 (dt, 1H, J=13.5, 3.9 Hz), 2.50-2.23 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a2e0575a19944e46b63914c692f309b1
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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