Ammonia → HCID 53955701, compound

HRID 1577998Notes

Reaction equation

HRID 1577998 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])(=O)C1C=CC=CC=1.CO.N>O>[SH:9][CH2:10][CH2:11][C:12]([N:14]1[C@@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 12773841HCID 12773841, compound

Product 1

HCID 53955701HCID 53955701, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

This product from Example 3 was added to a solution of methanol saturated with ammonia and was stirred at 25° C. for 2 hours. The solvent was evaporated off, leaving a solid which was stirred in water and filtered. The filtrate was extracted five times with diethyl ether and was acidified. The acidified solution was then extracted with methylene chloride, washed with brine, dried over magnesium sulfate and concentrated to a solid. This residue was extracted with hot hexane from which the title compound crystallized, m.p. 61°-64° C.

Workup

  1. customThe solvent was evaporated off
  2. customleaving a solid which
  3. filtrationfiltered
  4. extractionThe filtrate was extracted five times with diethyl ether
  5. extractionThe acidified solution was then extracted with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to a solid
  9. extractionThis residue was extracted with hot hexane from which the title compound
  10. customcrystallized

Sources & evidence

ORD record
ord-ae20c55804c9446da79ecf7fc6bf4478
Source dataset
uspto-grants-1981_09
Patent number
US04290952

Reaction notes

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