Methanol → HCID 86667779, compound

HRID 1484483Notes

Reaction equation

HRID 1484483 reaction equation
[N:1]([CH:4]([O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)[CH2:5][CH2:6][NH:7]C(=O)C(F)(F)F)=[N+:2]=[N-:3].CO.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:7][CH2:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86667778HCID 86667778, compound

Product 1

HCID 86667779HCID 86667779, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl 4-[(1-azido-3-trifluoroacetamidopropoxy)methyl]benzoate (220 mg; 0.61 mmol) was added to methanol (2.3 mL) and a solution of potassium carbonate (200 mg; 1.4 mmol) in H2O (1.1 mL). The mixture was vigorously stirred at room temperature for 3 h, diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtrated and evaporated. The residue was purified by silica column chromatography (DCM:MeCN 1:1+5% MeOH+1% TEA) to provide methyl 4-[(3-amino-1-azidopropoxy)methyl]benzoate as a liquid in a yield of 110 mg (68%). 1H-NMR (500 MHz, CDCl3): δ=1.78-2.02 ppm (m, 2H), 2.85 ppm (t, J=7.0 Hz, 2H), 3.91 ppm (s, 3H), 4.60 ppm (t, J=6.5 Hz, 1H), 4.62 ppm (d, J=12.5 Hz, 1H), 4.87 ppm (d, J=12.5 Hz, 1H); 13C-NMR (500 MHz, CDCl3): δ=37.79 (in [D6]DMSO this peak splits in two distinct signals with δ=37.92 ppm and 38.93 ppm), 52.21, 70.16, 90.40, 127.55, 129.80, 129.89, 142.17, 166.84 ppm. HRMS [+Scan]; calculated m/z for C12H17N4O3 265.1295; observed mass: 265.1292.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltrated
  5. customevaporated
  6. customThe residue was purified by silica column chromatography (DCM:MeCN 1:1+5% MeOH+1% TEA)

Sources & evidence

ORD record
ord-3b3c288bd76e4e0ea56f3c575f6d91fb
Source dataset
uspto-grants-2016_08
Patent number
US09422232B2

Reaction notes

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