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

HRID 383976Notes

Reaction equation

HRID 383976 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 (×2) and methanol (×2). 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 (×2) and methanol (×2)
  4. customevaporated

Sources & evidence

ORD record
ord-911bdb1510a94e4cb4d1bb04a90b2fb6
Source dataset
uspto-grants-2013_02
Patent number
US08367673B2

Reaction notes

Loading…