Hydrochloric Acid → HCID 67434993, compound

HRID 1946530Notes

Reaction equation

HRID 1946530 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[C:14]3[CH:15]([CH2:19][C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=3[N:12]=[C:11]2[CH:30]([CH3:32])[CH3:31])[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C(#N)C.O>[NH3:10].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[C:14]3[CH:15]([CH2:19][C:20]([OH:22])=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=3[N:12]=[C:11]2[CH:30]([CH3:32])[CH3:31])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58460176HCID 58460176, compound

Product 1

HCID 67434993HCID 67434993, compound

Reagents, catalysts & solvents 2

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

Procedure

Intermediate 66 (177 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 and the reaction mixture. 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. LC/MS, MH+ 361, Rt 2.01 mins (5 min system).

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-cbc0d784fc2f40b0b322d822bd4e18dd
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

Loading…