Lithiumtriethylborohydride → HCID 10309586, compound

HRID 1444085Notes

Reaction equation

HRID 1444085 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[N:14]=[C:15]([C:25](OC)=[O:26])[C:16]([C:21](OC)=[O:22])=[N:17][C:18]=1[O:19][CH3:20])(=[O:11])=[O:10].C([BH-](CC)CC)C.[Li+]>O1CCCC1>[OH:22][CH2:21][C:16]1[N:17]=[C:18]([O:19][CH3:20])[C:13]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])(=[O:10])=[O:11])=[N:14][C:15]=1[CH2:25][OH:26]

Participants

4

Reactant 2

HCID 23664628LithiumtriethylborohydrideHCID 59168171HCID 59168171, compound

Product 1

HCID 10309586HCID 10309586, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-{[(2,3-dichlorophenyl)sulphonyl]amino}-6-methoxypyrazine-2,3-dicarboxylic acid, dimethyl ester (Example 211b, 0.5 g) dissolved in anhydrous tetrahydrofuran (20 mL) at 0° C. was added a solution of lithium triethylborohydride (Super is hydride®) (5.55 mL of a 1M solution in tetrahydrofuran) and the resulting solution was stirred for 1 hour. The reaction was quenched by the addition of 1N hydrochloric acid (10 mL) and extracted into ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to afford an oil that was purified by chromatography on silica gel eluting with ethyl acetate/dichloromethane mixtures to afford the titled compound (0.201 g) as a foam.

Workup

  1. customThe reaction was quenched by the addition of 1N hydrochloric acid (10 mL)
  2. extractionextracted into ethyl acetate (2×20 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford an oil that
  7. customwas purified by chromatography on silica gel eluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-7f3d2b2c92f24255a7fda423c1e964a2
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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