Hydroxylamine → (2S,3S)-N,2-dihydroxy-5-methyl-3-({(2R)-2-methyl-4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)hexanamide

HRID 888224Notes

Reaction equation

HRID 888224 reaction equation
CC1(C)[O:6][C:5](=O)[C@H:4]([C@@H:8]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=3)[CH2:17][C@H:16]2[CH3:31])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[O:3]1.[NH2:33][OH:34]>CO.CO.C(#N)C>[OH:34][NH:33][C:5](=[O:6])[C@@H:4]([OH:3])[C@@H:8]([C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:24]=[CH:23][N:22]=2)[CH2:17][C@H:16]1[CH3:31])=[O:14])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 58487995HCID 58487995, compound

Product 1

HCID 11517633(2S,3S)-N,2-dihydroxy-5-methyl-3-({(2R)-2-methyl-4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)hexanamideYield 29.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

To a solution of (5S)-2,2-dimethyl-5-[(1S)-3-methyl-1-({(2R)-2-methyl-4-[4-(trifluoro methyl)pyridin-2-yl]piperazin-1-yl}carbonyl)butyl]-1,3-dioxolan-4-one (142 mg; 0.31 mmol; 1.0 eq.) in MeOH (5.0 mL) was added an aqueous solution of hydroxylamine (50%; 0.046 mL; 1.55 mmol; 5.0 eq.) and the resulting reaction mixture was stirred at RT for 4.5 h. Evaporation of the solvents gave an oil. This residue was taken up in MeOH/ACN (2 mL/1 mL) and purified by reverse-phase chromatography to give the title product (3) as a white powder (40 mg; 29.8%) as a single diastereoisomer. M−(ESI): 431.0; M+(ESI): 433.6. HPLC (condition C): Rt: 10.8 min (HPLC purity: 98.7%).

Workup

  1. customthe resulting reaction mixture
  2. customEvaporation of the solvents
  3. customgave an oil
  4. custompurified by reverse-phase chromatography

Sources & evidence

ORD record
ord-ff99b0ddaa1441a29b0348f79856ae9c
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

Loading…