Hydrochloric Acid → Lithium Chloride

HRID 538386Notes

Reaction equation

HRID 538386 reaction equation
FCCC[O:5][C:6]([C:8]1[C:13]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:12][C:11]([O:29][CH2:30][CH2:31][CH2:32][F:33])=[CH:10][N:9]=1)=[O:7].COC(C1C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC(OCCCF)=CN=1)=O.[Li+:64].[OH-].[ClH:66]>C1COCC1.C1(C)C=CC=CC=1>[C:25]([O:24][C:22]([N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=[C:11]([O:29][CH2:30][CH2:31][CH2:32][F:33])[N:12]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26].[Cl-:66].[Li+:64]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68107695HCID 68107695, compoundHCID 68108271HCID 68108271, compound

Product 2

HCID 433294Lithium ChlorideHCID 68108115HCID 68108115, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(di-tert-butoxycarbonyl-amino)-5-(3-fluoro-propoxy)-pyrazine-2-carboxylic acid 3-fluoro-propyl ester and 3-(di-tert-butoxycarbonyl-amino)-5-(3-fluoro-propoxy)-pyrazine-2-carboxylic acid methyl ester (395 mg, 0.92 mmol) in THF (10 ml) was added 0.5N LiOH (2.02 ml, 1.01 mmol) and the mixture was stirred for 5.5 h. To the reaction mixture was added 1N HCl (0.92 ml, 0.92 mmol) after stirring for 5 min toluene was added and the solvents were evaporated to provide the title compound together with lithium chloride as a light yellow solid. The mixture was used for coupling reactions without further purification.

Workup

  1. additionwas added
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-c3a58135743d458396a12e6baf29e53a
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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