Hydroxylamine → HCID 14860703, compound

HRID 1768683Notes

Reaction equation

HRID 1768683 reaction equation
[C:1]([NH:4][CH:5](Br)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].[NH2:17][OH:18]>C1COCC1>[C:1]([NH:4][CH:5]([NH:17][OH:18])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 14860701HCID 14860701, compound

Product 1

HCID 14860703HCID 14860703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

2-Acetamido-N-benzyl-2-bromoacetamide (prepared from 2-acetamido-N-benzyl-2-ethoxyacetamide (3.00 g, 12.0 mmol) and BBr3 (1M in CH2Cl2, 17.2 mL, 17.2 rental)) was dissolved in THF (250 mL), cooled (-10° C.), and then added dropwise (30 min) to a suspension of NH2OH (5-6 equiv) in THF (50 mL) at -10° C. The reaction mixture was stirred (30 min) at this temperature and then allowed to warm to room temperature (1 h). The insoluble materials were filtered and the filtrate was concentrated in vacuo. The residue was separated into two components by flash column chromatography on SiO2 gel (7.5% MeOH/CHCl3).

Workup

  1. additionadded dropwise (30 min)
  2. temperatureto warm to room temperature (1 h)
  3. filtrationThe insoluble materials were filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was separated into two components by flash column chromatography on SiO2 gel (7.5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-c05acc5e7d8748148a752e5b3baffc03
Source dataset
uspto-grants-1995_01
Patent number
US05378729

Reaction notes

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