Hydrochloric Acid → HCID 178523264, compound

HRID 36523Notes

Reaction equation

HRID 36523 reaction equation
C([S:4][CH2:5][CH:6]([C:17]([F:20])([F:19])[F:18])[C:7]([NH:9][CH2:10][CH2:11][C:12]1[NH:16][N:15]=[N:14][N:13]=1)=[O:8])(=O)C.O.Cl>[NH4+].[OH-]>[F:19][C:17]([F:18])([F:20])[CH:6]([CH2:5][SH:4])[C:7]([NH:9][CH2:10][CH2:11][C:12]1[NH:16][N:15]=[N:14][N:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178477117HCID 178477117, compound

Product 1

HCID 178523264HCID 178523264, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

The title compound of Example 26 (1.0 g., 3.2 mmol.) was dissolved at 0° C. under argon in 2.5 mL of a 1:1 concentrated NH4OH:H2O solution. The reaction mixture was stirred at 0° C. for minutes and then acidified with 5N HCl to pH 6 at 0° C. The product was extracted with ethyl acetate containing 5 percent methanol (3×) (200 mL portions). The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed through 50 g of Merck silica gel using a (3:3:94) methanol:acetic acid:methylene chloride solvent system. The appropriate fractions were combined and concentrated to yield 0.56 g of the title product, m.p. 182°-184° C.

Workup

  1. extractionThe product was extracted with ethyl acetate containing 5 percent methanol (3×) (200 mL portions)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed through 50 g of Merck silica gel using a (3:3:94) methanol
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-344517ee2f254031ae38fafb63374b08
Source dataset
uspto-grants-1995_05
Patent number
US05414017

Reaction notes

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