Water → HCID 66592918, compound

HRID 1091854Notes

Reaction equation

HRID 1091854 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[N:14]([CH3:16])[C:13]3[C:12](=[O:17])[N:11]([CH3:18])[CH2:10][CH2:9][C:8]=3[C:7]=2[C:6]([C:19]([OH:21])=[O:20])=[CH:5][CH:4]=1.[CH:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24](O)[CH:23]=1.CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][O:2][C:3]1[C:15]2[N:14]([CH3:16])[C:13]3[C:12](=[O:17])[N:11]([CH3:18])[CH2:10][CH2:9][C:8]=3[C:7]=2[C:6]([C:19]([O:21][C:24]2[CH:23]=[CH:22][C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=2)=[O:20])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66593034HCID 66593034, compound

Product 1

HCID 66592918HCID 66592918, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-methoxy-2,9-dimethyl-1-oxo-1,2,3,4-tetrahydro-β-carboline-5-carboxylic acid (from step 5) (1 mmol), p-nitrophenol (1.5 mmol), EDCI (1.5 mmol) and DMAP (0.1 mmol) in dry THF was stirred at r.t. for 18 h. Minimum water was then added and the precipitated p-nitrophenylester was filtered and washed with water and dried (50-60%).

Workup

  1. filtrationthe precipitated p-nitrophenylester was filtered
  2. washwashed with water
  3. customdried (50-60%)

Sources & evidence

ORD record
ord-56d3fddfe6a14e4986cff0b767597b40
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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