Benzylamine → HCID 18767786, compound

HRID 2300211Notes

Reaction equation

HRID 2300211 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:18][CH:17](OS(C3C=CC(OCCCC)=CC=3)(=O)=O)[CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH2:34]([NH:41][CH:17]1[CH2:16][N:15]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=2)(=[O:13])=[O:14])[CH2:18]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 86584413HCID 86584413, compound

Product 1

HCID 18767786HCID 18767786, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-Butoxy-benzenesulfonic acid 1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl ester (0.99 g, 2 mmol) in tetrahydrofuran (4 ml) was added benzylamine (0.86 g, 8 mmol) and the mixture was stirred at 100° C. for 5 days. It was then washed with hexanes, and the residue was extracted with ether. The ether solution was evaporated, and the residue was chromatographed (silica gel, ethyl acetate-hexanes/1:1)to give 0.40 g of an amber gum; MS (ES) m/z 375.0 (MH+); HRMS (ES) Calcd. for C20H27N2O3S (MH+): 375.1742, Found: 375.1743.

Workup

  1. washIt was then washed with hexanes
  2. extractionthe residue was extracted with ether
  3. customThe ether solution was evaporated
  4. customthe residue was chromatographed (silica gel, ethyl acetate-hexanes/1:1)to

Sources & evidence

ORD record
ord-c2ec4191209c412cb2f196ed59da8d55
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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