Triethylamine → HCID 69110274, compound

HRID 1359468Notes

Reaction equation

HRID 1359468 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([NH2:16])([C:13]([OH:15])=[O:14])[CH2:8]2.C(N(CC)CC)C.[C:24](=O)([O:40]N1C(=O)CCC1=O)[O:25][CH2:26][CH:27]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2>C(#N)C.O>[C:24]([CH:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1([NH2:16])[C:13]([OH:15])=[O:14])([O:25][CH2:26][CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[C:39]1=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:40]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145234HCID 22145234, compound

Product 1

HCID 69110274HCID 69110274, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-methoxy-2-aminotetraline-2-carboxylic acid (prepared according to Obrecht, D. et. al. Helv. Chim Acta. 1992, 75, 1666) (802 mg, 3.62 mmole), triethylamine (0.62 ml, 4.45 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 1.47 g, 4.36 mmole) in acetonitrile (25 ml) and water (25 ml) was stirred at room temperature for 30 hours. TLC analysis of the reaction indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (370 mg) and triethylamine (0.6 ml) were added and the mixture was stirred at room temperature for another 24 hours. The reaction mixture was concentrated in vacuo to remove most of the acetonitrile, acidified to pH˜3 with 10% aqueous citric acid solution, and the white emulsion was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. Filtration and concentration gave a crude oil which was purified by column chromatography (eluted with 1→3→5→10% methanol/methylene chloride) to give racemic Fmoc-5-methoxy-2-aminotetraline-2-carboxylic acid (1.14 g, 71% yield) as an off-white solid. HRMS (FAB): C27H26NO5 (M+H) calc. 444.1812; observed: 444.1814.

Workup

  1. stirringthe mixture was stirred at room temperature for another 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove most of the acetonitrile
  4. extractionthe white emulsion was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and concentration
  8. customgave a crude oil which
  9. customwas purified by column chromatography (eluted with 1→3→5→10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-792032858763471e907c2eb88a3d303e
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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