Hydrochloric Acid → HCID 69457928, compound

HRID 1351971Notes

Reaction equation

HRID 1351971 reaction equation
[NH2:1][C@H:2]([CH3:21])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C[Si](C)(C)NC(=O)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C@H:34]1[O:36][CH2:35]1.Cl.C(=O)([O-])O.[Na+]>CS(C)=O>[Cl:30][C:31]1[CH:32]=[C:33]([C@@H:34]([OH:36])[CH2:35][NH:1][C@H:2]([CH3:21])[CH2:3][C:4]2[C:12]3[C:7](=[C:8]([CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 516892Sodium BicarbonateHCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69457148HCID 69457148, compound

Product 1

HCID 69457928HCID 69457928, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-{3-[(2R)-2-aminopropyl]-1H-indol-7-yl}-N,N-diethylacetamide (1.0 g, 3.48 mmol) in dimethylsulfoxide (5 mL) is added N-trimethylsilylacetamide (0.50 g, 3.83 mmol), and the mixture is stirred at room temperature for 1 hour. To the reaction solution is added (R)-(+)-3-chlorostyrene oxide (0.89 mL, 6.96 mmol), and the mixture is stirred at 110° C. for 2 hours. After cooling, a 2 N hydrochloric acid (5 mL) is added to the mixture, and the mixture is stirred at room temperature for 0.5 hour. To the mixture are added a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and the mixture is extracted with chloroform. The organic layer is dried over anhydrous sodium sulfate and concentrated. The residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform) to give the title compound (0.90 g, yield: 59%).

Workup

  1. stirringthe mixture is stirred at 110° C. for 2 hours
  2. temperatureAfter cooling
  3. stirringthe mixture is stirred at room temperature for 0.5 hour
  4. extractiona saturated brine, and the mixture is extracted with chloroform
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform)

Sources & evidence

ORD record
ord-ea1f38e574da404c9d6b98ea9e454877
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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