Ammonia → HCID 20088287, compound

HRID 275492Notes

Reaction equation

HRID 275492 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][C:26](=[O:31])[C:27]([O:29]C)=O)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.[NH3:32].CO>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][C:26]([C:27]([NH2:32])=[O:29])=[O:31])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 20088275HCID 20088275, compound

Product 1

HCID 20088287HCID 20088287, compoundYield 93%

Conditions

Temperature
-78 °C

Procedure

A suspension of methyl N-[2-(3,4-dibenzyloxyphenyl)ethyl]oxamate (5.0 g, 11.9 mmol) in methanol (100 mL) contained in a Fischer-Porter pressure vessel under argon was cooled to -78° C. Ammonia (ca. 60 mL) was condensed into the vessel, the vessel was sealed and allowed to come to room temperature. The suspension was allowed to stir at room temperature under a pressure of approximately 60 psi for 17 h. The mixture was cooled to -78° C., the vessel was opened and the vigorously stirred suspension was allowed to come to room temperature under a stream of argon. After 1.5 h, the solvent was removed in vacuo and the solid was triturated with 20% methylene chloride/ether to provide a white solid (4.5 g, 93%): m.p. 187° C.

Workup

  1. customcondensed into the vessel
  2. customthe vessel was sealed
  3. customto come to room temperature
  4. temperatureThe mixture was cooled to -78° C.
  5. customto come to room temperature under a stream of argon
  6. waitAfter 1.5 h
  7. customthe solvent was removed in vacuo
  8. customthe solid was triturated with 20% methylene chloride/ether

Sources & evidence

ORD record
ord-157520853c144b7a8eb29179cb05a033
Source dataset
uspto-grants-1995_02
Patent number
US05393788

Reaction notes

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