Hydrochloric Acid → (R)-N-(4-Carbamimidoylphenyl)-2-hydroxy-2-{(R)-3-oxo-4-[4-(trifluoromethyl)phenyl]morpholin-2-yl}acetamide

HRID 876603Notes

Reaction equation

HRID 876603 reaction equation
C([O:4][C@H:5]([C@H:21]1[O:26][CH2:25][CH2:24][N:23]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:22]1=[O:37])[C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18]C(=O)O[N:15]=2)=[CH:10][CH:9]=1)(=O)C.N.CO.Cl>CCOCC>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:6](=[O:20])[C@H:5]([OH:4])[C@H:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[C:22]2=[O:37])=[CH:9][CH:10]=1)(=[NH:15])[NH2:18]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21705897Ammonia methanolHCID 136009057(R)-2-oxo-2-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenylamino)-1-((R)-3-oxo-4-(4-(trifluoromethyl)phenyl)morpholin-2-yl)ethyl acetate

Product 1

HCID 58181940(R)-N-(4-Carbamimidoylphenyl)-2-hydroxy-2-{(R)-3-oxo-4-[4-(trifluoromethyl)phenyl]morpholin-2-yl}acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The compound 96-1 (110 mg) was treated with 7 M NH3/MeOH (1 mL) and the mixture was stirred at RT for 1 h. After removal of the volatile materials on the rotavap, the residue was dissolved in MeOH (1 mL) and 3M HCl (0.25 ml). The resulting suspension was treated with a balloon of H2 over 10% Pd/C (30 mg) and stirred at RT for 2 h. The resulting mixture was filtered through Celite® and concentrated. The residue was purified by reverse phase HPLC to give EXAMPLE 96 which was converted to the HCl salt (88 mg) by treating with one equivalent HCl in ether and concentration on a rotavap.

Workup

  1. customAfter removal of the volatile materials on the rotavap
  2. dissolutionthe residue was dissolved in MeOH (1 mL)
  3. additionThe resulting suspension was treated with a balloon of H2 over 10% Pd/C (30 mg)
  4. stirringstirred at RT for 2 h
  5. filtrationThe resulting mixture was filtered through Celite®
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase HPLC
  8. customto give EXAMPLE 96 which

Sources & evidence

ORD record
ord-506331884e0f4f4fb5dcc73ebdef91e0
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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