Lithium hydroxide, monohydrate → HCID 69655655, compound

HRID 11637Notes

Reaction equation

HRID 11637 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:16][C:17]([N:19]1[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:21][C@H:20]1[CH3:34])=[O:18].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[C:8]([CH:13]=1)[CH2:7][NH:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 696552703-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamino)-propionic Acid Methyl Ester

Product 1

HCID 69655655HCID 69655655, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamino)-propionic acid methyl ester (0.035 g, 0.069 mmol) in tetrahydrofuran (0.2 mL), methanol (0.2 mL) and water (0.1 mL) was added lithium hydroxide monohydrate (0.015 g, 0.35 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then concentrated in vacuo and the resulting residue was dissolved in dichloromethane and treated with hydrogen chloride gas. The resulting white solid was washed with acetonitrile. The acetonitrile wash was concentrated to give the title compound as its hydrochloride salt (0.010 g, LRMS: 490.3).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane
  3. additiontreated with hydrogen chloride gas
  4. washThe resulting white solid was washed with acetonitrile
  5. washThe acetonitrile wash
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-622432d3bf8e4e35b4337c9306449914
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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