Hydroxylamine → HCID 58488026, compound

HRID 1677795Notes

Reaction equation

HRID 1677795 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:29]2[O:33]C(C)(C)O[C:30]2=[O:36])[C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:6][CH:5]=1)[CH3:2].[NH2:37][OH:38].O>CC(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C@@H:13]([C:14]([N:16]2[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)=[O:15])[C@H:29]([OH:33])[C:30]([NH:37][OH:38])=[O:36])=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 58487979HCID 58487979, compound

Product 1

HCID 58488026HCID 58488026, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (5S)-5-[(1R)-4-(4-ethoxyphenyl)-1-({4-[2-(2-thienyl)ethyl]-1-piperazinyl}carbonyl)butyl]-2,2-dimethyl-1,3-dioxolan-4-one (101 mg, 0.20 mmol) in iPrOH (3 mL) was added a 50% aqueous solution of hydroxylamine (60 μL) and the resulting mixture was stirred at RT for 1 hour. Then water (12 mL) was added and the resulting mixture was purified by reverse-phase chromatography (using a mixture of water and iPrOH with a ratio from 4:1 to 1:1 as eluent) to give 40 mg (42%) of the title compound as a white powder. M−(ESI): 488.4; M+(ESI): 490.4. HPLC, Rt: 2.5 min (purity: 97.0%).

Workup

  1. customthe resulting mixture was purified by reverse-phase chromatography (
  2. additiona mixture of water and iPrOH with a ratio from 4:1 to 1:1 as eluent)

Sources & evidence

ORD record
ord-58cbd6fa368148e79ec53f67d8ce0634
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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