N,N-Dimethylpropargylamine → HCID 58739194, compound

HRID 720266Notes

Reaction equation

HRID 720266 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[N:17][OH:18])[CH:11]=1)[CH3:9])(C)(C)C.[CH3:20][N:21]([CH3:25])[CH2:22][C:23]#[CH:24]>ClCCl>[CH3:20][N:21]([CH2:22][C:23]1[O:18][N:17]=[C:16]([C:12]2[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[CH:15]=[CH:14][CH:13]=2)[CH:24]=1)[CH3:25]

Participants

4

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 86592613HCID 86592613, compound

Product 1

HCID 58739194HCID 58739194, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-{1-[3-(hydroxyimino-methyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (260 mg, 1 mmol) in dichloromethane (5 mL) was added dimethylpropargylamine (323 μL, 3 mmol) followed by household bleach (5 mL). The reaction mixture was stirred vigorously at room temperature for 2 h, the two layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, the crude product was dissolved in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL), and the reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silica gel benzene sulfonic acid linked) to give the title product (200 mg, 82% yield) as yellow oil.

Workup

  1. customthe two layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe crude product was dissolved in CH2Cl2 (8 mL)
  6. stirringtrifluoroacetic acid (2 mL), and the reaction mixture was stirred at room temperature for 1 h
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by solid phase extraction (SCX cartridge, silica gel benzene sulfonic acid linked)

Sources & evidence

ORD record
ord-14932a2e3e85447e80f4971a2e51df53
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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