Triethylamine → HCID 67015961, compound

HRID 1888740Notes

Reaction equation

HRID 1888740 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC(C)C.[NH2:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1[NH2:40])[C:33]([O:35][CH3:36])=[O:34]>C1COCC1.C(OCC)(=O)C>[NH2:40][C:39]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=1[NH:29][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 2684712-N-Boc-aminopropionic acid

Product 1

HCID 67015961HCID 67015961, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-D,L-alanine (3.76 g, 19.9 mmol) and triethylamine (2.76 mL, 19.9 mmol) in THF (25 mL) was added 2-methylpropyl chlorocarbonate (2.58 mL, 19.9 mmol) under ice-cooling, and the mixture was stirred for 30 min. To this solution was added dropwise a solution of methyl 3,4-diaminobenzoate (3.00 g, 18.1 mmol) in THF (15 mL) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. This solution was applied to basic silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained residue was triturated with ethyl acetate to give the title compound (4.21 g, yield 69%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. washthe mixture was washed with 10% aqueous potassium carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-4977011e1d894aea8a202fa54dcbbaa3
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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