Cyclohexanesulfonyl chloride → Tert-butyl 2-(3-(cyclohexanesulfonamido)phenoxy)ethylcarbamate

HRID 716745Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH:19]1([S:25](Cl)(=[O:27])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([S:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=2)[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:27])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Reactant 2

HCID 237554Cyclohexanesulfonyl chloride

HCID 11557882tert-butyl N-[2-(3-aminophenoxy)ethyl]carbamate

Product 1

HCID 68523431Tert-butyl 2-(3-(cyclohexanesulfonamido)phenoxy)ethylcarbamate

Procedure

Sulfonation of tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) using cyclohexanesulfonyl chloride (8) following the method described in Example 1 gave tert-butyl 2-(3-(cyclohexanesulfonamido)phenoxy)ethylcarbamate (9) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 7.16 (t, J=8.0 Hz, 1H), 6.97 (t, J=6.0 Hz, 1H), 6.75-6.78 (m, 2H), 6.59-6.62 (m, 1H), 3.87 (t, J=5.6 Hz, 2H), 3.24 (q, J=6.0 Hz, 2H), 2.89-2.98 (m, 1H), 1.92-2.01 (m, 2H), 1.68-1.76 (m, 2H), 1.52-1.57 (m, 1H), 1.31-42 (m, 11H), 1.05-1.22 (m, 2H).

Sources & evidence

ORD record: ord-e90527a5949f45bbb8be8b1e85e2f068
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193669B2

Reaction notes

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