Acetyl chloride → HCID 49853709, compound

HRID 1400029Notes

Reaction equation

HRID 1400029 reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl.O>[C:31]([N:3]1[CH2:4][CH:5]2[C:1]([C:7]3[CH:8]=[CH:9][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:11][CH:12]=3)([CH2:6]2)[CH2:2]1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67515007HCID 67515007, compound2×

Product 1

HCID 49853709HCID 49853709, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (80 mg, 0.23 mmol) in DCM (2 mL) were added triethylamine (0.13 mL, 0.92 mmol) and acetyl chloride (0.02 mL, 0.34 mmol) at 0° C. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with water (10 mL) and extracted with DCM (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.83:9.17 MeOH:CHCl3) to provide the title compound (42 mg, 51%) as white solid.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 0.83:9.17 MeOH:CHCl3)

Sources & evidence

ORD record
ord-5082918687ad4af5b7a0630356ac4891
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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