Ammonia → HCID 51029937, compound

HRID 706298Notes

Reaction equation

HRID 706298 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH:21](O)=O.N>Cl>[NH:1]1[C:2]2[CH:3]=[C:4]([N:9]3[C@@H:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:12][O:11][C:10]3=[O:20])[CH:5]=[CH:6][C:7]=2[N:8]=[CH:21]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 284Formic AcidHCID 57488463HCID 57488463, compound

Product 1

HCID 51029937HCID 51029937, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

The (S)-3-(3,4-diaminophenyl)-4-phenyloxazolidin-2-one was dissolved in 2.5 mL of 5N aqueous hydrochloric acid and 0.25 mL of formic acid was added to the solution. The reaction was stirred at reflux for 1 h before the reaction was cooled down to 0° C. and the reaction mixture was neutralized with buffer (pH7) and conc. ammonia. The aqueous layer was than extracted by means of 25 mL dichloromethane three times. The organic layers were combined, dried, filtered and the solvent was removed under reduced pressure. The final product was purified by means of FPLC using chloroform-methanol gradient (0→10%). The product elutes at about 5% methanol.

Workup

  1. temperatureat reflux for 1 h before the reaction
  2. extractionthan extracted by means of 25 mL dichloromethane three times
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe final product was purified by means of FPLC

Sources & evidence

ORD record
ord-eb063204f85c4386b32cdf64e20ea656
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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