Triethylamine → HCID 49853917, compound

HRID 1400034Notes

Reaction equation

HRID 1400034 reaction equation
[OH:1][CH2:2][C:3]([N:5]1[CH2:10][CH:9]2[C:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]4=[O:27])=[CH:13][CH:12]=3)([CH2:8]2)[CH2:6]1)=[O:4].C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1COCC1.O>[CH2:39]([O:38][C:36](=[O:37])[O:1][CH2:2][C:3]([N:5]1[CH2:10][CH:9]2[C:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]4=[O:27])=[CH:13][CH:12]=3)([CH2:8]2)[CH2:6]1)=[O:4])[CH3:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 49853914HCID 49853914, compound

Product 1

HCID 49853917HCID 49853917, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-{4-[3-(2-hydroxy-acetyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-phenyl}-2-oxo-oxazolidin-5(S)-ylmethyl)-acetamide (Example X) (200 mg, 0.54 mmol) in THF (5 mL) were added triethylamine (0.19 mL, 1.35 mmol) and ethyl chloroformate (0.07 mL, 0.7 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, 0.3:9.7 MeOH:CHCl3) to provide the title compound (72 mg, 30%) 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, 0.3:9.7 MeOH:CHCl3)

Sources & evidence

ORD record
ord-dec169e3ff5c4b489914051b967fc662
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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