2-Propanesulfonyl chloride → Tert-butyl 2-(3-(1-methylethylsulfonamido)phenoxy)ethylcarbamate

HRID 716744Notes

Reaction equation

HRID 716744 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].[CH3:19][CH:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21]>>[CH3:19][CH:20]([S:22]([NH: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])(=[O:24])=[O:23])[CH3:21]

Participants

3

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 11557882tert-butyl N-[2-(3-aminophenoxy)ethyl]carbamate

Product 1

HCID 68524470Tert-butyl 2-(3-(1-methylethylsulfonamido)phenoxy)ethylcarbamate

Procedure

Sulfonation of tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) using propane-2-sulfonyl chloride following the method described in Example 1 gave tert-butyl 2-(3-(1-methylethylsulfonamido)phenoxy)ethylcarbamate (7) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 7.17 (t, J=8.0 Hz, 1H), 6.97 (t, J=6.0 Hz, 1H), 6.76-6.79 (m, 2H), 6.60-6.62 (m, 1H), 3.16-3.30 (m, 3H), 1.35 (s, 9H), 1.19 (d, J=6.8 Hz, 6H).

Sources & evidence

ORD record
ord-360d0a2753a94e399cd17cf0c78a4a61
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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