Sodium hydride → Isohexane ethyl acetate

HRID 1444038Notes

Reaction equation

HRID 1444038 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:20](Br)=[N:19][C:18]([Br:22])=[CH:17][N:16]=1)(=[O:13])=[O:12].[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH2:35][OH:36])=[O:29])(C)(C)[CH3:24]>COCCOC>[C:28]([O:27][CH2:23][CH3:24])(=[O:29])[CH3:4].[CH3:34][CH2:33][CH2:32][CH:31]([CH3:35])[CH3:4].[Br:22][C:18]1[N:19]=[C:20]([O:36][CH2:35][C@@H:31]2[CH2:32][CH2:33][CH2:34][NH:30]2)[C:15]([NH:14][S:11]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:4]=2[Cl:3])(=[O:13])=[O:12])=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 550865tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 591682192,3-Dichloro-N-(3,5-dibromo-2-pyrazinyl)benzenesulphonamide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 59168149HCID 59168149, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (0.026 g of a 60% dispersion in oil) was added to a mixture of 2,3-dichloro-N-(3,5-dibromo-2-pyrazinyl)benzenesulphonamide (Example 31a) (0.1 g) and 2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (0.088 g) in 1,2-dimethoxyethane (2 mL). After 0.5 h, the reaction mixture was partitioned between 2N hydrochloric acid and ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound protected with the BOC (tert-butoxycarbonyl) group (0.11 g) as an oil. This product was dissolved in dichloromethane (6 mL) and trifluoroacetic acid (2 mL). After 2 h, toluene was added and the solution evaporated to dryness. Crystallisation from diethyl ether gave the product as a white solid (0.083 g).

Workup

  1. customthe reaction mixture was partitioned between 2N hydrochloric acid and ethyl acetate
  2. dry with materialThe organic solution was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-7c06c85ca4554e6086199e18e8483498
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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