Water → HCID 69457249, compound

HRID 1351965Notes

Reaction equation

HRID 1351965 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C@H:12]([N:14]1[CH2:18][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[O:16][C:15]1=[O:26])[CH3:13].C(N(CC)CC)C.[C:34](Cl)(=[O:37])[CH2:35][CH3:36].O>O1CCCC1>[Cl:25][C:21]1[CH:20]=[C:19]([C@H:17]2[O:16][C:15](=[O:26])[N:14]([C@H:12]([CH3:13])[CH2:11][C:7]3[C:6]4[C:10](=[C:2]([NH:1][C:34](=[O:37])[CH2:35][CH3:36])[CH:3]=[CH:4][CH:5]=4)[NH:9][CH:8]=3)[CH2:18]2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 69458120HCID 69458120, compound

Product 1

HCID 69457249HCID 69457249, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5R)-3-((1R)-2-(7-amino-1H-indol-3-yl)-1-methylethyl)-5-(3-chlorophenyl)-1,3-oxazolidin-2-one (28.4 mg, 0.0768 mmol) in tetrahydrofuran (1 mL) are added triethylamine (13.5 μL, 0.0969 mmol) and propionyl chloride (8 μL, 0.0921 mmol) under nitrogen atmosphere, and the mixture is stirred at room temperature for 1 hour. The reaction solution is poured into water, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated, and the obtained crude product is purified by preparative thin layer chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (34.3 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 anhydrous sodium sulfate
  4. customThe solvent is evaporated
  5. customthe obtained crude product
  6. customis purified by preparative thin layer chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-44397f83b9104faebe59addc51aa42b9
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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