Hydrochloric Acid → HCID 58465742, compound

HRID 1842463Notes

Reaction equation

HRID 1842463 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][N:16]2[N:20]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:22]=[C:15]2[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2].[OH-].[Li+].O.Cl>C1COCC1.CO>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][N:16]2[N:20]=[C:21]([C:23]([OH:25])=[O:24])[CH:22]=[C:15]2[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 58465583HCID 58465583, compound

Product 1

HCID 58465742HCID 58465742, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-[(2-nitrophenyl)sulfonyl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate (0.143 g, 0.362 mmol) was dissolved in a mixture of THF (4 mL) and methanol (1 mL) and to the solution was added 1.0 M of lithium hydroxide in water (1.5 mL, 1.5 mmol). The resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated, and the residue was dissolved in water (5 mL) and neutralized with 1.0 M hydrochloric acid in water (1.5 mL, 1.5 mmol). The resulting precipitate was collected via vacuum filtration to afford Intermediate 20 as a white solid (0.1166 g, 88%). LC-MS: (FA) ES+395.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water (5 mL)
  3. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-aab7462f5d9945e2ac600ed08937ccc2
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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