Trifluoroacetic acid → HCID 59125435, compound

HRID 1062566Notes

Reaction equation

HRID 1062566 reaction equation
Cl.[NH2:2][C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.C(=O)(O)[O-].[Na+].[CH3:22][C:23]1[C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[S:26][C:27]=1[CH:28]=O.F[C:35](F)(F)C(O)=O>>[CH3:35][O:15][C:14]([C@@H:3]1[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:28]([C:27]2[S:26][C:25]3[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=3[C:23]=2[CH3:22])[NH:2]1)=[O:16]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 134608Tryptophan--hydrogen chloride (1/1)HCID 516892Sodium BicarbonateHCID 5199183-Methylbenzo(b)thiophene-2-carboxaldehyde

Product 1

HCID 59125435HCID 59125435, compoundYield 38%

Procedure

An aqueous solution of (S)-(−)-tryptophan hydrochloride (1.45 g, 5.7 mmol) was made alkaline with a saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed once with aqueous sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. The free base-was dissolved in chloroform (50 mL) and treated with 3-methylbenzo[b]thiophene-2-carbaldehyde (1.0 g, 5.7 mmol) and trifluoroacetic acid (21.2 mmol, 1.32 g). The resulting mixture then was heated to reflux for 3 hours. The solution was cooled to room temperature, washed once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo to provide a mixture of two diastereomers. The isomers were separated by chromatography (silica gel, 30% ethyl acetate:hexanes) to give 700 mg (38%) of (1R,3S)-1-(3-methylbenzo[b]thiophen-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediate 5) and 400 mg (19%) of (1S;3S)-1-(3-methylbenzo[b]thiophen-2-yl)-2,3,4,9-tetra-hydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediate 6).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed once with aqueous sodium chloride solution
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe free base-was dissolved in chloroform (50 mL)
  7. temperatureThe resulting mixture then was heated
  8. temperatureto reflux for 3 hours
  9. washwashed once with saturated sodium bicarbonate solution
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto provide
  14. additiona mixture of two diastereomers
  15. customThe isomers were separated by chromatography (silica gel, 30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-38a43fb066784b9abf20cbd4ac5b274a
Source dataset
uspto-grants-2005_11
Patent number
US06962918B2

Reaction notes

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