4-Chlorobenzenesulfonyl chloride → 1-(4-Chloro-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide

HRID 2407540Notes

Reaction equation

HRID 2407540 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.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>>[C:20]1([CH2:19][CH2:18][CH2:17][NH:16][C:15]([N:13]2[CH2:12][C:11]3([N:8]([S:34]([C:31]4[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=4)(=[O:36])=[O:35])[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 73984-Chlorobenzenesulfonyl chlorideHCID 866823516-(3-Phenyl-propylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

Product 1

HCID 715550461-(4-Chloro-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 4-chlorobenzene-1-sulfonyl chloride into the title compound which was obtained as a colorless sticky solid (25 mg, 17%). MS m/e: 434 (M+H)+.

Sources & evidence

ORD record
ord-f814c407cdeb410b99fe1153116e9ccd
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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