Triethylamine → HCID 69110469, compound

HRID 1825274Notes

Reaction equation

HRID 1825274 reaction equation
[CH2:1]([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)[CH3:2].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]([CH2:1][CH3:2])[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 8471TriethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 22145255HCID 22145255, compound

Product 1

HCID 69110469HCID 69110469, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-ethyl-2-aminotetraline-2-carboxylic acid (765 mg, 3.49 mmole), triethylamine (1.0 ml, 7.17 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 1.79 g, 5.31 mmole) in acetonitrile (40 ml) and water (40 ml) was stirred at room temperature for 2 days. 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 twice with methylene chloride, twice with ethyl acetate. The methylene chloride extracts were washed with water, brine and dried over magnesium sulfate. The ethyl acetate extracts 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 2→5→8% methanol/methylene chloride) to give racemic Fmoc-5-ethyl-2-aminotetraline-2-carboxylic acid (330 mg, 21% yield) as a white solid. HRMS (FAB): C28H28NO4 (M+H) calc. 442.2018; observed: 442.2010.

Workup

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

Sources & evidence

ORD record
ord-64b31a7d92a04c1ba424e56a46f27d3e
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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