Ammonia → HCID 178498182, compound

HRID 1088608Notes

Reaction equation

HRID 1088608 reaction equation
C[O:2][CH2:3][PH:4]([O:6][C@@H:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:8]([NH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[O:9])=[O:5].C(O)(C)C.N.O>CC(C)=O>[OH:2][CH2:3][PH:4]([O:6][C@@H:7]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:8]([NH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[O:9])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 3776IsopropanolHCID 178502584HCID 178502584, compound

Product 1

HCID 178498182HCID 178498182, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The methyl ester product from part (b) (2.3 g., 5.88 mmole) is suspended in acetone (7 ml.) at room temperature. Trimethylamine is bubbled in for about 20 minutes to saturate the mixture. The reaction vessel is sealed, and the mixture is heated to about 95° and is stirred overnight. The volatiles are evaporated, and the residue is partitioned between ethyl acetate and 5% potassium bisulfate. The organic layer is washed once with brine, dried (Na2SO4), filtered, and the volatiles are evaporated to give 1.86 g. of 4-[[(S)-2=[(hydroxymethylphosphinyl)oxy]-1-oxo-3-phenylpropyl]amino]benzoic acid, methyl ester. TLC (silica gel; isopropanol:ammonia:water, 7:2:1) Rf =0.62.

Workup

  1. customTrimethylamine is bubbled in for about 20 minutes
  2. concentrationto saturate the mixture
  3. customThe reaction vessel is sealed
  4. temperaturethe mixture is heated to about 95°
  5. customThe volatiles are evaporated
  6. customthe residue is partitioned between ethyl acetate and 5% potassium bisulfate
  7. washThe organic layer is washed once with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe volatiles are evaporated
  11. customto give 1.86 g

Sources & evidence

ORD record
ord-9845a1dd5bec4543bac3bd8924aff667
Source dataset
uspto-grants-1990_10
Patent number
US04963539

Reaction notes

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