Triethylamine → HCID 69110315, compound

HRID 1359473Notes

Reaction equation

HRID 1359473 reaction equation
[CH3:1][N:2]([CH3:17])[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.C(N(CC)CC)C.[C:25](=O)([O:41]N1C(=O)CCC1=O)[O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2>C(#N)C.O>[C:25]([CH:8]1[C:9]2[C:4](=[C:3]([N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1([NH2:16])[C:13]([OH:15])=[O:14])([O:26][CH2:27][CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:41]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145285HCID 22145285, compound

Product 1

HCID 69110315HCID 69110315, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-dimethylamino-2-aminotetraline-2-carboxylic acid (1.33 g, 2.15 mmole theoretical), triethylamine (0.40 ml, 2.87 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 0.92 g, 2.73 mmole) in acetonitrile (10 ml) and water (10 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 (400 mg) and triethylamine (0.2 ml) were 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 and the almost neutral mixture was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate. Filtration and concentration gave a crude which was purified by column chromatography (eluted with 2.5→6→10→15→20% methanol/methylene chloride) to give racemic Fmoc-5-dimethylamino-2-aminotetraline-2-carboxylic acid (602 mg, 61% yield over 2 steps) as an off-white solid. HRMS (FAB): C28H28N2O4 (M) calc. 456.2049; observed: 456.2056.

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 almost neutral mixture was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration
  8. customgave a crude which
  9. customwas purified by column chromatography (eluted with 2.5→6→10→15→20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-37960ce68bf34271a8d9427541d8087d
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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