Hydrochloric Acid → HCID 178523264, compound

HRID 36505Notes

Reaction equation

HRID 36505 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 5 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 x) (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 x) (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-412ed8a4da234bef8ff5f71486aedeb2
Source dataset
uspto-grants-1995_05
Patent number
US05414013

Reaction notes

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