Triethylamine → HCID 69109997, compound

HRID 1825267Notes

Reaction equation

HRID 1825267 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8]([NH2:17])([C:14]([OH:16])=[O:15])[CH2:9]2)[CH3:2].C(N(CC)CC)C.[C:25](=O)([O:41]N1C(=O)CCC1=O)[O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2>C(#N)C.O>[C:25]([CH:9]1[C:10]2[C:5](=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:7][C:8]1([NH2:17])[C:14]([OH:16])=[O:15])([O:26][CH2:27][CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:41]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145259HCID 22145259, compound

Product 1

HCID 69109997HCID 69109997, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-ethoxy-2-aminotetraline-2-carboxylic acid (2.22 g, 9.44 mmole), triethylamine (2.00 ml, 14.3 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 4.81 g, 14.3 mmole) in acetonitrile (75 ml) and water (75 ml) was stirred at room temperature for two days. TLC analysis of the reaction indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (645 mg) and triethylamine (1.0 ml) was added and the mixture was stirred at room temperature for another day. 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 extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate. Filtration and concentration gave a crude oil which was purified by column chromatography (eluted with 3→5→10% methanol/methylene chloride) to give racemic Fmoc-5-ethoxy-2-aminotetraline-2-carboxylic acid (4.66 g, >quantitative yield) as a white solid. HRMS (FAB): C28H28NO5 (M+H) calc. 458.1967; observed: 458.1985.

Workup

  1. stirringthe mixture was stirred at room temperature for another day
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove most of the acetonitrile
  4. extractionthe white emulsion 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 3→5→10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-7cf4df7a7d9f4c2d9e39bb6fca5ac947
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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