Dimethylformamide → HCID 140407445, compound

HRID 1636928Notes

Reaction equation

HRID 1636928 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14]N)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([NH:23][C:24](C1C=CNN=1)=[N:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:22])([CH3:19])([CH3:18])[CH3:17].C[N:39](C)C=O>>[C:29]([O:28][C:26]([N:25]([O:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:24]([NH:23][C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22])=[NH:39])=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 13983481Benzyl (2-(aminooxy)ethyl)carbamateHCID 178454276N,N'-bis-BOC-pyrazole carboxamidine

Product 1

HCID 140407445HCID 140407445, compoundYield 93%

Procedure

To a solution of 2-(benzyloxycarbonylamino)ethoxyamine (780 mg, 3.7 mmol), as prepared in the preceding step, in N,N-dimethylformamide (20 mL) was added [N,N'-di(tert-butoxycarbonyl)]amidinopyrazole (1.25 g, 4.0 mmol). The mixture was stirred at room temperature overnight, the solvent was evaporated under high vacuum. The residue was purified by flash column chromatography (0-5% ethyl acetate in methylene chloride) to give the title compound as a colorless oil (1.55 g, 93%). 1H-NMR (300 MHz, CDCl3) δ9.08 (s, 1H), 7.67 (s, 1H), 7.33 (m, 5H), 6.21 (br s, 1H), 5.21 (br s, 1H), 5.11 (s, 2H), 4.12 (t, J=4.8 Hz, 2H), 3.54 (q, J=4.9 Hz, 2H), 1.49 (s, 9H), 1.46 (s, 9H).

Workup

  1. customthe solvent was evaporated under high vacuum
  2. customThe residue was purified by flash column chromatography (0-5% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-aac3e98ffcd84c229e442817fc768267
Source dataset
uspto-grants-2000_03
Patent number
US06037356

Reaction notes

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