Methanesulfonyl chloride → HCID 178483643, compound

HRID 967214Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>>[C:1]([O:5][C:6]([N:7]([CH3:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][CH2:18][O:19][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:15][CH2:16]1)=[O:20])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 178483640HCID 178483640, compound

Product 1

HCID 178483643HCID 178483643, compound

Procedure

In analogy to the procedures described in examples 11.13, 11.14 and 11.15, trans-{2-[4-(2-hydroxy-ethyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester was reacted with methanesulfonyl chloride to give trans-methanesulfonic acid 2-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-ethyl ester, which was subsequently treated with 4N hydrogen chloride in dioxan to yield trans-methanesulfonic acid 2-[4-(2-methylamino-ethyl)-cyclohexyl]-ethyl ester HCl salt as colorless solid; treatment of the trans-methanesulfonic acid 2-[4-(2-methylamino-ethyl)-cyclohexyl]-ethyl ester HCl salt with 4-chloro-benzene sulphonyl chloride then yielded trans-methanesulfonic acid 2-(4-{2-[(4-chloro-benzenesulfonyl)-methyl-amino]-ethyl}-cyclohexyl)-ethyl ester as colorless oil, MS: 438 (MH+, 1Cl).

Sources & evidence

ORD record: ord-6a9f17ad6657453f82a4fe38be7e95bb
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953806B2

Reaction notes

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