Triethylamine → HCID 58375893, compound

HRID 1942483Notes

Reaction equation

HRID 1942483 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH:29]([CH3:31])[CH3:30])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH2:25][C:26](O)=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]([CH:29]([CH3:31])[CH3:30])[C@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C@@H:15]([CH2:25][CH2:26][OH:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 58376294HCID 58376294, compound

Product 1

HCID 58375893HCID 58375893, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(2R,5R)-5-[[(benzyloxy)carbonyl](isopropyl)amino]-1-(tert-butoxycarbonyl)-piperidin-2-yl]acetic acid (8.0 g) in tetrahydrofuran (100 mL) was added triethylamine (7.7 mL), and thereto was added ethyl chloroformate (3.5 mL) under ice-cooling. After the mixture was stirred under ice-cooling for one hour, the insoluble materials were removed by filtration. To the filtrate was added dropwise a solution of sodium borohydride (3.5 g) in water (30 mL) under ice-cooling with stirring. Then, the mixture was stirred at room temperature for one hour. To the mixture was added an aqueous potassium hydrogen sulfate solution under ice-cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to give the title compound (6.7 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. customthe insoluble materials were removed by filtration
  4. additionTo the filtrate was added dropwise a solution of sodium borohydride (3.5 g) in water (30 mL) under ice-
  5. temperaturecooling
  6. stirringwith stirring
  7. stirringThen, the mixture was stirred at room temperature for one hour
  8. additionTo the mixture was added an aqueous potassium hydrogen sulfate solution under ice-
  9. temperaturecooling
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated under reduced pressure
  14. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4586f64df8e34e028ebfadfe83bfc386
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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