Triethylamine → HCID 69111269, compound

HRID 1825269Notes

Reaction equation

HRID 1825269 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9]([NH2:18])([C:15]([OH:17])=[O:16])[CH2:10]2)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26](=O)([O:42]N1C(=O)CCC1=O)[O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2>C(#N)C.O>[C:26]([CH:10]1[C:11]2[C:6](=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1([NH2:18])[C:15]([OH:17])=[O:16])([O:27][CH2:28][CH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[C:41]1=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:42]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145244HCID 22145244, compound

Product 1

HCID 69111269HCID 69111269, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-isopropoxy-2-aminotetraline-2-carboxylic acid (3.48 g, 5.98 mmole theoretical), triethylamine (1.10 ml, 7.89 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 2.62 g, 7.77 mmole) in acetonitrile (30 ml) and water (30 ml) was stirred at room temperature for one day. TLC analysis of the reaction indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (500 mg) 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 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 1→2→5→8% methanol/methylene chloride) to give racemic Fmoc-5-isopropoxy-2-aminotetraline-2-carboxylic acid (0.50 g, 18% yield over 2 steps) as a white solid. HRMS (FAB): C29H30NO5 (M+H) calc. 472.2124; observed: 472.2117.

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 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 1→2→5→8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-254def57fd3b4fe08ebad3baceb0fbec
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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