Hydroxylamine → HCID 11653205, compound

HRID 1677779Notes

Reaction equation

HRID 1677779 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]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[O:3]1.[NH2:28][OH:29]>CC(O)C>[OH:29][NH:28][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]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58487957HCID 58487957, compound

Product 1

HCID 11653205HCID 11653205, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (5S)-2,2-dimethyl-5-((1S)-3-methyl-1-{[4-(2-pyridinyl)-1-piperazinyl]carbonyl}butyl)-1,3-dioxolan-4-one (250 mg; 0.67 mmol; 1.0 eq.) in iPrOH (5 mL) was added an aqueous solution of hydroxylamine (50%; 0.195 mL; 3.35 mmol; 5.0 eq.) and the resulting reaction mixture was stirred at RT for 2.5 h. After evaporation of the solvents, the crude mixture was purified by reverse-phase chromatography to give the title compound (1) as a white powder (74 mg; 31%). M−(ESI): 349.2; M+(ESI): 351.1. HPLC: Rt: 1.3 min (HPLC purity: 100%).

Workup

  1. customthe resulting reaction mixture
  2. customAfter evaporation of the solvents
  3. customthe crude mixture was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-bdf682a669bb4271b15ee737bf6d8ed7
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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