Ethanol → HCID 13037302, compound

HRID 1732134Notes

Reaction equation

HRID 1732134 reaction equation
[F:1][C:2]1[CH:16]=[C:15]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:4][CH:3]=1.C=O.S(=O)(=O)(O)O.[CH2:24](O)C>O>[F:1][C:2]1[CH:16]=[C:15]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:7]1[CH2:24][NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]2=1

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 688357L-5-Fluorotryptophan

Product 1

HCID 13037302HCID 13037302, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 111 mg of 5-fluoro-L-tryptophan, 50 mg of 35% formalin, 0.8 ml of 0.1N sulfuric acid, 0.4 ml of ethanol and 0.3 ml of water is stirred at room temperature for 24 hours. The precipitates are collected by filtration, washed with water and ethanol and then dried. 80 mg of (3S)-6-fluoro-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid are obtained as white powder. Yield: 69%

Workup

  1. filtrationThe precipitates are collected by filtration
  2. washwashed with water and ethanol
  3. customdried

Sources & evidence

ORD record
ord-90a52b734fcd45d4b20e77c30c2db266
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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