4-Chlorobenzenesulfonyl chloride → 1-(4-Chloro-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid 2,4-dichloro-benzylamide

HRID 2407544Notes

Reaction equation

HRID 2407544 reaction equation
C(OC([N:8]1[C:11]2([CH2:14][N:13]([C:15](=[O:26])[NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[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>>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:15]([N:13]1[CH2:12][C:11]2([N:8]([S:34]([C:31]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)(=[O:36])=[O:35])[CH2:9][CH2:10]2)[CH2:14]1)=[O:26]

Participants

3

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 866823536-(2,4-Dichloro-benzylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

Product 1

HCID 715550481-(4-Chloro-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid 2,4-dichloro-benzylamide

Procedure

In analogy to the experimental procedure of example 6b) 6-(2,4-Dichloro-benzylcarbamoyl)-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 an off-white solid (41 mg, 23%). MS m/e: 474 (M+H)+.

Sources & evidence

ORD record
ord-cd92cc17c75749b687c5ca3f9a485d1d
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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