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

HRID 1475973Notes

Reaction equation

HRID 1475973 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:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])(=[O:19])[CH3:18]>>[C:17]([O:20][N:21]([S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[S:2]([CH3:1])(=[O:4])=[O:3])(=[O:13])=[O:12])[C:22](=[O:23])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 10954788Benzyl (acetyloxy)carbamate

Product 1

HCID 53240987Benzyl (acetyloxy){[2-(methylsulfonyl)phenyl]sulfonyl}carbamate

Procedure

Benzyl (acetyloxy){[2-(methylsulfonyl)phenyl]sulfonyl}carbamate (50) is prepared from 2-methylsulfonylbenzenesulfonyl chloride, sodium hydride and [(benzyloxy) carbonyl]amino acetate according to Scheme 2. (0.33 g, 28%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.21-8.47 (2H, m), 7.79-7.88 (1H, m), 7.65-7.74 (1H, m), 7.30-7.41 (3H, m), 7.16-7.24 (2H, m), 5.18 (2H, br. s.), 3.31 (3H, s), 2.29 (3H, s).

Sources & evidence

ORD record
ord-e7429e2f8481477599e735f1ae4478fe
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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