methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride → HCID 66696501, compound

HRID 929331Notes

Reaction equation

HRID 929331 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]([NH:14][CH:15]([C:27]([O:29]C)=[O:28])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=3)[NH:19][CH:18]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[OH:9].Cl.COC(=O)[C@H](CC1C2C(=CC=C(O)C=2)NC=1)N>O.[OH-].[Na+].CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]([NH:14][CH:15]([C:27]([OH:29])=[O:28])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=3)[NH:19][CH:18]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 2

HCID 24802218methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochlorideHCID 66696497HCID 66696497, compound

Product 1

HCID 66696501HCID 66696501, compoundYield 15.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-(3-Methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-methoxycarbonylethyl]-2-propenamide synthesized from 5-hydroxy-L-tryptophan methyl ester hydrochloride (704 mg, 2.6 mmol) in the same manner as in Example 18 was dissolved in a mixed solvent of water (11.8 ml), 2.5N NaOH aqueous solution (11.8 ml), and N,N-dimethylformamide (23.6 ml) without purification, and the mixture was stirred at room temperature overnight. The reaction solvent was concentrated under reduced pressure, cooled to 0° C., and adjusted with 6N aqueous HCl solution to pH 1 to 2. The solution was extracted three times with ethyl acetate (30 ml), and the organic layer was washed with 3N HCl (20 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, and purified by preparative thin-layer chromatography (PTLC, eluent: chloroform:methanol=3:1) to give 3-(3-methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-hydroxycarbonylethyl]-2-propenamide (147 mg, yield 15.4%) as a powder.

Workup

  1. concentrationThe reaction solvent was concentrated under reduced pressure
  2. temperaturecooled to 0° C.
  3. extractionThe solution was extracted three times with ethyl acetate (30 ml)
  4. washthe organic layer was washed with 3N HCl (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customMagnesium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. custompurified by preparative thin-layer chromatography (PTLC, eluent: chloroform:methanol=3:1)

Sources & evidence

ORD record
ord-6958cd95d78743dea790711b5d950fc8
Source dataset
uspto-grants-2016_03
Patent number
US09295624B2

Reaction notes

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