Triethylamine → HCID 69110373, compound

HRID 1825264Notes

Reaction equation

HRID 1825264 reaction equation
[Cl: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]([Cl: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 22145240HCID 22145240, compound

Product 1

HCID 69110373HCID 69110373, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of racemic 5-chloro-2-aminotetraline-2-carboxylic acid (402 mg, 1.78 mmole), triethylamine (0.38 ml, 2.73 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 904 mg, 2.68 mmole) in acetonitrile (20 ml) and water (20 ml) was stirred at room temperature for two days. TLC analysis of the reaction after two days indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (0.12 g) and triethylamine (0.1 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→6→8% methanol/methylene chloride) to give racemic Fmoc-5-chloro-2-aminotetraline-2-carboxylic acid (540 mg, 68% yield) as a white solid. HRMS (EI): C26H22ClNO4 (M) calc. 447.1237; observed: 447.1234.

Workup

  1. customTLC analysis of the reaction after two days
  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 three times with ethyl acetate
  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 3→6→8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-57fa7fda1f77402ba6899df5d6abbe4f
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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