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

HRID 2407542Notes

Reaction equation

HRID 2407542 reaction equation
C(OC([N:8]1[C:11]2([CH2:14][N:13]([C:15](=[O:27])[NH:16][C:17]34[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]5)[CH2:18]3)[CH2:24]4)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>>[C:17]12([NH:16][C:15]([N:13]3[CH2:14][C:11]4([N:8]([S:35]([C:32]5[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=5)(=[O:37])=[O:36])[CH2:9][CH2:10]4)[CH2:12]3)=[O:27])[CH2:18][CH:19]3[CH2:25][CH:23]([CH2:22][CH:21]([CH2:20]3)[CH2:26]1)[CH2:24]2

Participants

3

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 866823526-(Adamantan-1-ylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

Product 1

HCID 715550471-(4-Chloro-benzenesulfonyl)-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid adamantan-1-ylamide

Procedure

In analogy to the experimental procedure of example 6b) 6-(Adamantan-1-ylcarbamoyl)-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 sticky solid (29 mg, 35%). MS m/e: 450 (M+H)+.

Sources & evidence

ORD record
ord-6286e86ad9994f3c8db2e1c8b5ce52a4
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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