4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (1R,2R)-2-benzyloxycarbonylamino-cyclohexylmethyl Ester

HRID 1592325Notes

Reaction equation

HRID 1592325 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][O:18][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 24720936Benzyl trans-(2-hydroxymethyl)cyclohexylcarbamate

Product 1

HCID 86599633toluene-4-sulfonic acid (1R,2R)-2-benzyloxycarbonylamino-cyclohexylmethyl EsterYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (1R,2R)-(2-hydroxymethylcyclohexyl)-carbamic acid benzyl ester (6.0 g, 22.8 mmol) in pyridine (35 mL) was stirred on an ice-acetone bath and treated with toluene-4-sulfonyl chloride (4.78 g, 25.1 mmol). The reaction was stirred on an ice-water bath for 3 hours, then ice-cold water (35 mL) was added slowly. The mixture was diluted further with ice water and the resulting slurry was stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water, and dried under vacuum to provide a white powdery solid (9.1 g, 96%).

Workup

  1. stirringthe resulting slurry was stirred at room temperature for 1 hour
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3bd942723daf460f91405608f7a5bef2
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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