Triethylamine → HCID 69456513, compound

HRID 1351940Notes

Reaction equation

HRID 1351940 reaction equation
Cl.[CH2:2]([N:4]([CH2:30][CH3:31])[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C@H:17]([NH:19][CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[OH:22])[CH3:18])=[O:6])[CH3:3].C(N(CC)CC)C.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:30]([N:4]([CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C@H:17]([N:19]1[CH2:20][C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[O:22][C:40]1=[O:42])[CH3:18])=[O:6])[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 69459319HCID 69459319, compound

Product 1

HCID 69456513HCID 69456513, compoundYield 247.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxy-ethylamino]propyl}-1H-indole-7-carboxylic acid diethylamide.hydrochloride (47 mg, 0.1 mmol) and triethylamine (139 μL, 1 mmol) in tetrahydrofuran (3 mL) is added triphosgene (12 mg, 0.04 mmol), and the mixture is stirred at room temperature for 4 hours. To the mixture is added a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel column chromatography (methanol/chloroform=1/50) to give 3-{(2R)-2-[(5R)-5-(3-chlorophenyl)-2-oxooxazolidin-3-yl]propyl}-1H-indole-7-carboxylic acid diethylamide (45 mg, yield: 100%).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography (methanol/chloroform=1/50)

Sources & evidence

ORD record
ord-b5e3d13b0dbe4425a257a57b12491903
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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