Lithium Hydroxide → N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucine

HRID 2108708Notes

Reaction equation

HRID 2108708 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH:16][C@H:17]([C:22]([O:24]C)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Li+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH:16][C@H:17]([C:22]([OH:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68843329methyl N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate

Product 1

HCID 68847309N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucineYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate (520 mg) in methanol (5 ml) was added a solution of lithium hydroxide (91 mg) in water (3 ml). After stirring vigorously for 24 hours the solvent was removed in vacuo. The residue was diluted with water (10 ml) then neutralised with 2N hydrochloric acid. This solution was applied to an Oasis™ cartridge (2×6 g) and eluted with water (x2) and methanol (x2). The required fractions were combined and evaporated to afford N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucine (478 mg).

Workup

  1. customwas removed in vacuo
  2. additionThe residue was diluted with water (10 ml)
  3. washeluted with water (x2) and methanol (x2)
  4. customevaporated

Sources & evidence

ORD record
ord-7adb6cd985e045ce827509b808ff40e3
Source dataset
uspto-grants-2009_04
Patent number
US07514437B2

Reaction notes

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