Triethylamine → HCID 69110181, compound

HRID 1825271Notes

Reaction equation

HRID 1825271 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6]([NH2:15])([C:12]([OH:14])=[O:13])[CH2:7]2.C(N(CC)CC)C.[C:23](=O)([O:39]N1C(=O)CCC1=O)[O:24][CH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2>C(#N)C.O>[C:23]([CH:7]1[C:8]2[C:3](=[C:2]([CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][C:6]1([NH2:15])[C:12]([OH:14])=[O:13])([O:24][CH2:25][CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 221452712-Amino-5-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 69110181HCID 69110181, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-methyl-2-aminotetraline-2-carboxylic acid (1.05 g, 5.12 mmole), triethylamine (0.93 ml, 6.67 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 2.24 g, 6.64 mmole) in acetonitrile (30 ml) and water (30 ml) was stirred at room temperature for 2 days. TLC analysis of the reaction indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (520 mg) was 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 twice with methylene chloride. 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 2→5→8% methanol/methylene chloride) to give racemic Fmoc-5-methyl-2-aminotetraline-2-carboxylic acid (1.62 g, 74% yield) as an light brown solid. HRMS (FAB): C27H26NO4 (M+H) calc. 428.1862; observed: 428.1844.

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 twice with methylene chloride
  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 2→5→8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-ebd5d2d5bbca433b85acd713715d20bd
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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