Hydrochloric Acid → HCID 71205745, compound

HRID 1946532Notes

Reaction equation

HRID 1946532 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]([C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:7]2[CH:17]([CH2:21][C:22]([O:24]CC3C=CC=CC=3)=[O:23])[CH2:18][CH2:19][CH2:20][C:6]=2[N:5]=1)[CH3:3].[OH-].[Na+].Cl>CO.C(#N)C.O>[NH3:5].[CH3:3][CH:2]([C:4]1[N:8]([C@@H:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:7]2[CH:17]([CH2:21][C:22]([OH:24])=[O:23])[CH2:18][CH2:19][CH2:20][C:6]=2[N:5]=1)[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58460175HCID 58460175, compound

Product 1

HCID 71205745HCID 71205745, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Intermediate 67 (224 mg) was dissolved in methanol (4 mL). NaOH (2 mL, 6.60 mmol) was added to the stirred reaction mixture as a 3.3 N aqueous soln. After stirring overnight the reaction mixture was conc in vacuo and taken up in acetonitrile/water. The soln was taken to pH4-5 by the addition of 2 M aqueous HCl and loaded onto an SCX column. After washing with water and acetonitrile, the product was eluted with 2 M ammonia soln in methanol. The washing were conc in vacuo to afford the ammonium salt of the desired product (84 mg).

Workup

  1. washAfter washing with water and acetonitrile
  2. washthe product was eluted with 2 M ammonia soln in methanol

Sources & evidence

ORD record
ord-d7c24f1739264fe686561c2bddc7a00b
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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