Triethylamine → HCID 67015830, compound

HRID 1888728Notes

Reaction equation

HRID 1888728 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[OH:40])[C:33]([O:35][CH3:36])=[O:34]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1[OH:40])[C:33]([O:35][CH3:36])=[O:34])=[O:13])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 62365Isobutyl chloroformateHCID 2684712-N-Boc-aminopropionic acid

Product 1

HCID 67015830HCID 67015830, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-D,L-alanine (3.40 g, 17.9 mmol) and triethylamine (2.50 mL, 17.9 mmol) in THF (20 mL) was added 2-methylpropyl chlorocarbonate (2.33 mL, 17.9 mmol) under ice-cooling, and the mixture was stirred for 1 hr. To this solution was added dropwise a solution of methyl 3-amino-4-hydroxybenzoate (3.00 g, 17.9 mmol) in THF (10 mL) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 0.5N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was triturated with hexane-chloroform (1:1) to give the title compound (2.57 g, yield 42%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 days
  3. washthe mixture was washed with 0.5N hydrochloric acid 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 hexane-chloroform (1:1)

Sources & evidence

ORD record
ord-04db2f5d0ef94013b0b226a047b0fe69
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…