Lithium hydroxide, monohydrate → HCID 69655354, compound

HRID 11690Notes

Reaction equation

HRID 11690 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][NH:5][C:6]([C:8]1[C:9]([NH:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:7].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:14][C:12]1[CH:13]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:35])=[O:2])=[O:7])[C:9]([NH:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[N:10][CH:11]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69655399[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic Acid Methyl Ester

Product 1

HCID 69655354HCID 69655354, compoundYield 52.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic acid methyl ester (0.043 g, 0.085 mmol) in tetrahydrofuran (1 mL), methanol (1 mL) and water (0.25 mL) was added lithium hydroxide monohydrate (0.018 g, 0.43 mmol). The reaction was stirred overnight. The reaction was then concentrated in vacuo, diluted with dichloromethane and passed through a fritted funnel. The filtrate was treated with saturated hydrogen chloride in diethyl ether and the white precipitate formed was collected by filtration to give the title compound (0.022 g, LRMS: 492.2).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. custompassed through a fritted funnel
  4. additionThe filtrate was treated with saturated hydrogen chloride in diethyl ether
  5. customthe white precipitate formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c4bdb46ab996423f929805ab86e19afc
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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