1-(Methoxymethyl)cyclopropane-1-sulfonamide → N-Propyl-1-sulfamoylcyclopropane-1-carboxamide

HRID 1818764Notes

Reaction equation

HRID 1818764 reaction equation
C(NC(=O)O)(C)(C)C.[CH2:9]([NH:12][C:13]([C:15]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:17][CH2:16]1)=[O:14])[CH2:10][CH3:11].COCC1(S(N)(=O)=O)CC1>>[CH2:9]([NH:12][C:13]([C:15]1([S:18]([NH2:21])(=[O:19])=[O:20])[CH2:17][CH2:16]1)=[O:14])[CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 224992771-(Methoxymethyl)cyclopropane-1-sulfonamideHCID 667532941-Propylcarbamoylcyclopropanesulfonamide tert-butylcarbamate

Product 1

HCID 22499348N-Propyl-1-sulfamoylcyclopropane-1-carboxamideYield 50%

Procedure

This compound was obtained in an optimized 50% yield from 1-propylcarbamoylcyclopropanesulfonamide tert-butylcarbamate (from Step B.3.a) according to the procedure described for the synthesis of 1-methoxymethylcyclopropylsulfonamide (Step B.1.b), except that no chromatography was used as the material was recrystallized from the minimum amount of CH2Cl2/hexanes: 1H NMR (CDCl3) δ 0.15 (m, 2H), 0.51 (m, 2H), 1.01 (m, 2H), 1.34 (m, 3H), 1.86 (d, J=7.0 Hz, 2H), 4.83 (s, 2H); 13C NMR (CDCl3) δ 4.65, 7.74, 11.26, 35.62, 41.21; LRMS m/z 193 (M++NH4).

Workup

  1. customwas recrystallized from the minimum amount of CH2Cl2/hexanes

Sources & evidence

ORD record
ord-2c668ec6f28146e48a7d163df08803dc
Source dataset
uspto-grants-2009_10
Patent number
US07601686B2

Reaction notes

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