Triethylamine → HCID 14326883, compound

HRID 2232891Notes

Reaction equation

HRID 2232891 reaction equation
[CH:1]1([CH:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:8][C:9](Cl)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O:22][C:23](=[O:26])[CH2:24][NH2:25])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[O:10]=[C:9]([NH:25][CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])[CH2:8][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151417Glycine tert-butyl esterHCID 21282942HCID 21282942, compound

Product 1

HCID 14326883HCID 14326883, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A stirred solution of 3,3-dicyclohexylpropionyl chloride (6.1 g, 0.063 mol) in 70 ml of chloroform was treated portionwise at 7°-12° C. with a solution of 8.3 g (0.063 mol) of glycine tert-butyl ester and 8.9 ml (0.064 mol) of triethylamine in 30 ml of chloroform. After the addition, the solution was stirred at room temperature for 2 hours, kept overnight, refluxed for 0.5 hours, cooled, washed with water (5×25 ml), dried (magnesium sulfate), and the solvent removed on a rotary evaporator, to give a light yellow viscous oil. The latter, which crystallized partly on standing, was dissolved in 50 ml of boiling hexane, cooled, seeded, and rubbed; a crystalline solid gradually separated. After crystallizing at room temperature and cooling overnight, the voluminous colorless solid was filtered, washed with cold hexane and air-dried (13.3 g, melting point 72°-74° C. s, 69° C.).

Workup

  1. additionAfter the addition
  2. waitkept overnight
  3. temperaturerefluxed for 0.5 hours
  4. temperaturecooled
  5. washwashed with water (5×25 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent removed on a rotary evaporator
  8. customto give a light yellow viscous oil
  9. customThe latter, which crystallized partly
  10. dissolutionwas dissolved in 50 ml of boiling hexane
  11. temperaturecooled
  12. customa crystalline solid gradually separated
  13. customAfter crystallizing at room temperature
  14. temperaturecooling overnight
  15. filtrationthe voluminous colorless solid was filtered
  16. washwashed with cold hexane
  17. customair-dried (13.3 g, melting point 72°-74° C. s, 69° C.)

Sources & evidence

ORD record
ord-7a292112bc2349bdb71268ae0a821c3d
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

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