Dichloromethane → HCID 21258547, compound

HRID 635380Notes

Reaction equation

HRID 635380 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12]([CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:31]CCl>FC(F)(F)C(O)=O>[ClH:31].[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12]([CH2:21][CH2:22][NH2:23])=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 11133773HCID 11133773, compound

Product 1

HCID 21258547HCID 21258547, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the above protected tryptamine (2.1 g, in a mixture of dichloromethane and trifluoroacetic acid (1:1; 60 ml) was allowed to stand at room temperature for 3 h. The solvents were removed under vacuum and the residue was azeotroped with toluene-methanol (5:1; 100 ml). The residue was dissolved in 4N sodium hydroxide solution (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organic solutions were washed with brine (1×50 ml), dried (Na2SO4) and concentrated. The hydrochloride salt was prepared and recrystallised from acetonitrile to give 1.53 g of the title compound; mp 117°-120° C.; δH (360 MHz, D2O) 7.81 (2H, d, J=7.5 Hz), 7.74 (1H, d, J=9.0 Hz), 7.56 (1H, s), 7.54 (1H, t, J=7.5 Hz), 7.41 (2H, t, J=8.1 Hz), 7.00 (1H, d, J=2.3 Hz), 6.89 (1H, dd, J=9.0 and 2.3 Hz), 6.89 (1H, dd, J=9.0 and 2.3 Hz), 3.78 (3H, s),3.29 (2H, t, J=7.6 Hz), 3.01 (2H, t, J=7.6 Hz); m/z (ES) 331 (M++1). (Found: C, 54.07; H, 5.39; N, 7.41. C17H18N2O3S.1.0HCl.0.6 H2O requires: C, 54.06; H, 5.39; N, 7.42%).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was azeotroped with toluene-methanol (5:1; 100 ml)
  3. dissolutionThe residue was dissolved in 4N sodium hydroxide solution (50 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic solutions were washed with brine (1×50 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-957183c9bf434c958476cd6adf88e86e
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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