2-Trifluoromethylbenzenesulphonyl chloride → 1-(2-Trifluoromethyl-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide

HRID 2281683Notes

Reaction equation

HRID 2281683 reaction equation
C(OC([N:8]1[C:11]2([CH2:14][N:13]([C:15](=[O:26])[NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36]>>[C:20]1([CH2:19][CH2:18][CH2:17][NH:16][C:15]([N:13]2[CH2:12][C:11]3([N:8]([S:35]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[C:28]([F:27])([F:39])[F:40])(=[O:37])=[O:36])[CH2:9][CH2:10]3)[CH2:14]2)=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 866823516-(3-Phenyl-propylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

Product 1

HCID 715550501-(2-Trifluoromethyl-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide

Procedure

In analogy to the experimental procedure of example 6b) 6-(3-phenyl-propylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester instead of tert-butyl 1-(2,4-dichlorobenzylcarbamoyl)-1,6-diazaspiro[3.3]heptane-6-carboxylate was converted using 2-trifluoromethylbenzene-1-sulfonyl chloride instead of 4-chlorobenzene-1-sulfonyl chloride into the title compound which was obtained as an off-white solid (38 mg, 25%). MS m/e: 468 (M+H)+.

Sources & evidence

ORD record
ord-83079117ae264e14bd74e72d82485f67
Source dataset
uspto-grants-2015_09
Patent number
US09139593B2

Reaction notes

Loading…