Triethylamine → HCID 69110641, compound

HRID 1359465Notes

Reaction equation

HRID 1359465 reaction equation
[Br: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]([Br: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 8471Triethylamine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145258HCID 22145258, compound

Product 1

HCID 69110641HCID 69110641, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture of racemic 5-bromo-2 aminotetraline-2-carboxylic acid (882 mg, 3.27 mmole), triethylamine (0.60 ml, 4.30 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 1.32 g, 3.91 mmole) in acetonitrile (30 ml) and water (30 ml) was stirred at room temperature overnight. TLC analysis of the reaction the next day indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (0.25 g), triethylamine (0.6 ml) and acetonitrile (5 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 twice with methylene chloride. 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 2→5→10% methanol/methylene chloride) to give racemic Fmoc-5-bromo-2 aminotetraline-2-carboxylic acid (1.09 g, 68% yield) as a white solid. HRMS (FAB): C26H22BrNNaO4 (M+Na) calc. 514.0630; observed: 514.0643.

Workup

  1. customTLC analysis of the reaction the next day
  2. stirringthe mixture was stirred at room temperature for another day
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove most of the acetonitrile
  5. extractionthe white emulsion extracted twice with methylene chloride
  6. washThe combined organic layers 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→10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-860fbaefcd94436a96cdb854972dce28
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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