Sodium hydride → HCID 53241086, compound

HRID 1475979Notes

Reaction equation

HRID 1475979 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:7](Cl)(=[O:9])=[O:8].[H-].[Na+].[CH3:13][C:14]([CH3:27])([CH3:26])[C:15]([O:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16]>>[CH3:13][C:14]([CH3:27])([CH3:26])[C:15]([O:17][N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[S:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[Br:1])(=[O:9])=[O:8])=[O:16]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 300008[(tert-Butoxy)carbonyl]amino 2,2-dimethylpropanoateHCID 136755983-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 53241086HCID 53241086, compound

Procedure

N-[(tert-Butoxy)carbonyl]3-bromothiophene-2-sulfonamido 2,2-dimethylpropanoate (58) is synthesised from 3-bromothiophene-2-sulfonyl chloride (synthesised according to the method detailed in Bioorganic and Medicinal Chemistry Letters 1996, 6, 2651-2656), sodium hydride and [(tert-Butoxy)carbonyl]amino 2,2-dimethylpropanoate according to Scheme 2. (0.2 g, 12%), 1H NMR (500 MHz, DMSO-d6) δ ppm 8.25 (1H, d, 5.2 Hz), 7.44 (1H, d, 5.2 Hz), 1.39 (9H, s), 1.29 (9H, s).

Workup

  1. customsynthesised

Sources & evidence

ORD record
ord-5d02febe1fe7428e9a2c5574a4601eb8
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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