Triethylamine → HCID 67619232, compound

HRID 1075674Notes

Reaction equation

HRID 1075674 reaction equation
[Na+].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:20]=[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:30][C:31]([O-])=[O:32])[C:22]2=[O:34])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.[CH3:76][O:77][C:78](=[O:82])[C@H:79]([CH3:81])[NH2:80]>ClCCl>[CH3:76][O:77][C:78](=[O:82])[C@H:79]([CH3:81])[NH:80][C:31](=[O:32])[CH2:30][N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21](=[CH:20][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)[C:22]1=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 2733257Alanine methyl ester hydrochlorideHCID 67558328HCID 67558328, compound

Product 1

HCID 67619232HCID 67619232, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-(8-benzyloxyquinol-5-ylmethylen)-2-oxindol-1-yl] acetic acid sodium salt (50 mg, 0.11 mmol), benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (50 mg, 0.10 mmol) and triethylamine (11 mg, 0.11 mmol) in dichloromethane (10 ml) was added L-alanine methyl ester hydrochloride (20 mg, 0.14 mmol) and the mixture was stirred for 2 h at room temperature. Then dichloromethane was added, the organic layer washed 3 times with water, dried over sodium sulfate and concentrated under vacuum. The residue was chromatographed on silica gel using as eluant ethylacetate/cyclohexane (8:2) to give 45 mg (78.5% yield) of title compound.

Workup

  1. washthe organic layer washed 3 times with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was chromatographed on silica gel using as eluant ethylacetate/cyclohexane (8:2)

Sources & evidence

ORD record
ord-36f2c3f2b1834eeeba1fed24327a2a8c
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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