Sodium hydride → Benzyl {[2-(methylsulfonyl)phenyl]sulfonyl}(propanoyloxy)carbamate

HRID 1475975Notes

Reaction equation

HRID 1475975 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])(=[O:4])=[O:3].[H-].[Na+].[C:17]([O:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:20])[CH2:18][CH3:19]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:22]([O:21][C:17](=[O:20])[CH2:18][CH3:19])[C:23](=[O:24])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:13])=[O:12])(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 53881541[(Benzyloxy)carbonyl]amino propanoate

Product 1

HCID 53241080Benzyl {[2-(methylsulfonyl)phenyl]sulfonyl}(propanoyloxy)carbamate

Procedure

Benzyl {[2-(methylsulfonyl)phenyl]sulfonyl}(propanoyloxy)carbamate (51) is prepared from 2-methylsulfonylbenzenesulfonyl chloride, sodium hydride and [(benzyloxy)carbonyl]-amino propanoate according to Scheme 2. (0.56 g, 50%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.39 (1H, d, 7.9 Hz), 8.35 (1H, d, 7.9 Hz), 7.80-7.86 (1H, m), 7.68-7.73 (1H, m), 7.30-7.39 (3H, m), 7.18-7.23 (2H, m), 5.17 (2H, br. s.), 3.30 (3H, s), 2.58 (2H, br. s.), 1.23 (3 H, t, 7.5 Hz).

Sources & evidence

ORD record
ord-b5375029b1b64aa593a24ca1de416239
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

Loading…