O-methylhydroxylammonium chloride → HCID 67768684, compound

HRID 864096Notes

Reaction equation

HRID 864096 reaction equation
[OH:1][NH:2][N:3]=[CH:4][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13](=[O:34])[C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19](=[O:33])[C@@H:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:7][CH2:6]1.[CH3:35]O[NH3+].[Cl-]>CN1CCCC1=O.CCOCC>[CH3:35][O:1][NH:2][N:3]=[CH:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:11][NH:12][C:13](=[O:34])[C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19](=[O:33])[C@@H:20]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 67768813HCID 67768813, compound

Product 1

HCID 67768684HCID 67768684, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of Example 3 Part D aminonitrile (0.34 g, 0.74 mmol) in 3.0 mL of 1-methyl-2-pyrrolidinone was added methoxyamine.HCl (0.18 g, 216 mmol). This reaction solution was immersed into a 85° C. oil bath. The bath temperature was slowly raised up no 130° C. in 80 min. The reaction solution was stirred at 130° C. for 2 h and cooled to room temperature. The solution was diluted with 30 mL of ether and the solution was decanted. The remaining oily residue was purified by preparative HPLC to give 250 mg (51%) of title compound.

Workup

  1. customwas immersed into a 85° C.
  2. temperaturecooled to room temperature
  3. customthe solution was decanted
  4. customThe remaining oily residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2d4bd43b1feb4fd2930a400197690d7b
Source dataset
uspto-grants-1996_10
Patent number
US05561146

Reaction notes

Loading…