Lithium hydroxide, monohydrate → HCID 21043692, compound

HRID 11630Notes

Reaction equation

HRID 11630 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:23][C@H:22]1[CH3:35])=[O:20])=[O:8].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH2:23][C@H:22]2[CH3:35])=[O:20])=[C:10]([NH:9][C:7](=[O:8])[NH:6][CH2:5][CH2:4][C:3]([OH:36])=[O:2])[CH:15]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 696553713-[3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-ureido]-propionic Acid Methyl Ester

Product 1

HCID 21043692HCID 21043692, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-ureido]-propionic acid methyl ester (0.057 g, 0.11 mmol) in tetrahydrofuran (3 mL), methanol (3 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.023 g, 0.55 mmol). The reaction was stirred at ambient temperature overnight, concentrated in vacuo, taken up in methanol, passed through an ion exchange column and then treated with hydrogen chloride gas to give the title compound as its hydrochloride salt (0.035 g, LRMS: 507.2).

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with hydrogen chloride gas

Sources & evidence

ORD record
ord-f75693f6867e4644b7b4bb511c63c3fc
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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