Lithium Hydroxide → HCID 21072688, compound

HRID 1372876Notes

Reaction equation

HRID 1372876 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]=[CH:17][C:18]([C:21]([NH:23][C:24]3[CH:39]=[C:38]([C:40]([O:42]C)=[O:41])[CH:37]=[CH:36][C:25]=3[C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[O:22])=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]=[CH:17][C:18]([C:21]([NH:23][C:24]3[CH:39]=[C:38]([C:40]([OH:42])=[O:41])[CH:37]=[CH:36][C:25]=3[C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[O:22])=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21072689HCID 21072689, compound

Product 1

HCID 21072688HCID 21072688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[5-(4-t-butoxycarbonylhexahydro-1,4-diazepin-1-yl)pyrazin-2-ylcarbonylamino]-4-methoxycarbonyl-N-(5-chloropyridin-2-yl)benzamide (Example P10, 0.610 g, 1 mmol) in THF (6 mL) and water (2 mL) was added lithium hydroxide (0.240 g), and the solution was stirred overnight. THF was evaporated off under vacuum, and the remaining aqueous layer was acidified to pH 2 with 0.1 N HCl before it was extracted with ethyl acetate (3×20 mL), dried over magnesium sulfate and the solvent evaporated. This crude product was used as such for deprotection in the next step.

Workup

  1. customTHF was evaporated off under vacuum
  2. extractionwas extracted with ethyl acetate (3×20 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-09024bc64c674cce9cdfb3b966767c95
Source dataset
uspto-grants-2007_01
Patent number
US07160878B2

Reaction notes

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