Acetyl chloride → HCID 68709063, compound

HRID 2282558Notes

Reaction equation

HRID 2282558 reaction equation
[CH2:1]([O:8][CH2:9][C@@:10]12[CH2:22][CH2:21][CH2:20][N:11]1[C@@H:12](C(Cl)(Cl)Cl)[O:13][C:14]2=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(Cl)(=O)C>CO>[CH3:12][O:13][C:14]([C@:10]1([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:22][CH2:21][CH2:20][NH:11]1)=[O:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10942334Sodium MethoxideHCID 44603824HCID 44603824, compound

Product 1

HCID 68709063HCID 68709063, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Intermediate 85b (6.39 g, 17.9 mmol) and sodium methoxide (580 mg, 10.8 mmol) in MeOH (100 mL) was stirred at RT for 18 h. The mixture was cooled to 0° C., then acetyl chloride (28.4 g, 359 mmol) added. This mixture was stirred at reflux for 1 h, then cooled and concentrated in vacuo. The residue was divided, applied to SCX-2 cartridges (3×70 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave the title compound as a pale yellow oil (3.92 g, 87%). 1H NMR (400 MHz, CDCl3): 1.62-1.86 (3H, m), 1.07-2.13 (1H, m), 2.48 (1H, br s), 2.93-3.11 (2H, m), 3.69-3.78 (4H, m), 4.53 (1H, d, J 12.9), 4.55 (1H, d, J 12.9), 7.21-7.37 (5H, m).

Workup

  1. temperatureat reflux for 1 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. washwashed with MeOH
  5. washThe product was eluted with 2M NH3 in MeOH
  6. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-5bdb2280ed404f96aa961c0185b9ff6d
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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