Ammonia → HCID 57018033, compound

HRID 544555Notes

Reaction equation

HRID 544555 reaction equation
[CH:1]1([CH2:5][N:6]2[CH2:24][CH2:23][C@:13]34[C:14]5[C:15]6[O:22][CH:12]3[C:11]3(OCC[O:25]3)[CH2:10][CH2:9][C@@:8]4([F:29])[C@H:7]2[CH2:20][C:19]=5[CH:18]=[CH:17][C:16]=6[OH:21])[CH2:4][CH2:3][CH2:2]1.N>C(O)(=O)C(O)=O>[CH:1]1([CH2:5][N:6]2[CH2:24][CH2:23][C@:13]34[C:14]5[C:15]6[O:22][CH:12]3[C:11](=[O:25])[CH2:10][CH2:9][C@@:8]4([F:29])[C@H:7]2[CH2:20][C:19]=5[CH:18]=[CH:17][C:16]=6[OH:21])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57101162HCID 57101162, compound

Product 1

HCID 57018033HCID 57018033, compound

Reagents, catalysts & solvents 1

HCID 971Oxalic AcidSolvent

Procedure

17'-(Cyclobutylmethyl)-4',5'-epoxy-14'-fluorospiro-[1,3-dioxolane-2,6'-morphinan]-3'-ol (1.3 g) was added to a solution of oxalic acid (4.8 g in 80 ml of water) and heated at reflux for a period of 18 hours. The reaction mixture was cooled, and then basified with ammonia to pH 9.2. The precipitated solids were collected by filtration, washed with water, and air dried. The crude material melted at 100° with slight softening and sintering at 93°. The infrared spectrum indicated the presence of a carbonyl group (C=O), 1700 cm-1.

Workup

  1. temperatureheated
  2. temperatureat reflux for a period of 18 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitated solids were collected by filtration
  5. washwashed with water, and air
  6. customdried
  7. customsintering at 93°

Sources & evidence

ORD record
ord-cc37a2e4a77a42eb9e803c9da7df7808
Source dataset
uspto-grants-1984_05
Patent number
US04451470

Reaction notes

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