Hydroxylamine → HCID 72954426, compound

HRID 1727254Notes

Reaction equation

HRID 1727254 reaction equation
[NH2:1][OH:2].C([O:5][C:6](=O)[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17](=[O:37])[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)C>CO>[OH:2][NH:1][C:6]([CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:17](=[O:37])[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[CH:13][CH:14]=1)=[O:5]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 68841846HCID 68841846, compound

Product 1

HCID 72954426HCID 72954426, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.76 M NH2OH in MeOH (1.23 mL) was added the compound (150 mg, 0.31 mmol) from the process (1-2), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated, and the residue was dissolved in 1 N HCl aqueous solution (pH 5). The solid precipitated was collected by filtration, dried under vacuum, and crystallized from MeOH/CH2Cl2/ether to afford the titled compound (67 mg, 46%) as a pale brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 1 N HCl aqueous solution (pH 5)
  3. customThe solid precipitated
  4. filtrationwas collected by filtration
  5. customdried under vacuum
  6. customcrystallized from MeOH/CH2Cl2/ether

Sources & evidence

ORD record
ord-8b38dda51c0846cb88c14d4d8210db11
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

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