Triethylamine → HCID 178491192, compound

HRID 1631444Notes

Reaction equation

HRID 1631444 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:32][CH2:33][C:34]([CH3:39])([CH3:38])[C:35](Cl)=[O:36]>ClCCl>[Cl:32][CH2:33][C:34]([CH3:39])([CH3:38])[C:35]([N:8]([C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])[CH2:13][CH2:14]1)[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=1)=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 178491122HCID 178491122, compound

Product 1

HCID 178491192HCID 178491192, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 15A (200 mg, 0.598 mmol) in dichloromethane (5 mL) was treated with triethylamine (0.208 mL, 1.495 mmol), followed by slow addition of 3-chloro-2,2-dimethyl propanoyl chloride (0.155 mL, 1.196 mmol) at room temperature. After stirring for 2 h, reaction was judged complete by LCMS. It was washed with water, and the organics were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by Isco silica column (24 g) eluted with ethyl acetate:hexane, 0%-100%. Concentration of the appropriate fractions yielded 15B (226 mg, 83% yield) as a white foam. MS (ES): m/z=453.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.02 (d, 2H, J=8.5 Hz); 6.75 (d, 2H, J=8.5 Hz); 4.41 (s, 2H); 4.22-4.30 (m, 1H); 3.88-3.98 (m, 1H); 3.72 (s, 3H); 3.69 (s, 2H); 3.19-3.30 (m, 1H); 1.92-2.02 (m, 2H); 1.01-1.69 (m, 23H).

Workup

  1. customreaction
  2. washIt was washed with water
  3. dry with materialthe organics were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by Isco silica column (24 g)
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-df47d0bf113b4779a9d22c02c712060c
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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