Triethylamine → HCID 22800293, compound

HRID 1439703Notes

Reaction equation

HRID 1439703 reaction equation
[CH2:1](N(CC)CC)C.[C:8](=[O:24])([O-])[O:9][C:10]1[CH:15]=C(Cl)C(Cl)=C(C(C)(C)C)[C:11]=1Cl.[CH3:25][C@H:26]1[CH2:30][CH2:29][NH:28][C@@H:27]1[C:31]([OH:33])=[O:32]>C(O)(C)(C)C.O>[C:10]([O:9][C:8]([N:28]1[CH2:29][CH2:30][C@H:26]([CH3:25])[C@H:27]1[C:31]([OH:33])=[O:32])=[O:24])([CH3:11])([CH3:15])[CH3:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724879(2S,3S)-3-methylpyrrolidine-2-carboxylic AcidHCID 86585469HCID 86585469, compound

Product 1

HCID 22800293HCID 22800293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Triethylamine (3.5 ml) and t-butyl-2,4,5-trichlorophenyl carbonate (3.5 g) were added to a solution of trans-3-methyl-L-proline (1.25 g) in t-butanol (12 ml) and water (8 ml). The mixture was heated to 60° for 2 hours, evaporated, the residue dissolved in 1 N sodium bicarbonate solution (50 ml) and the solution washed with ether. Excess solid citric acid was added, the product extracted into ethyl acetate, the combined extracts dried (Na2SO4) and evaporated giving a crude crystalline product (1.6 g). Recrystallisation from ethyl acetate/light petroleum (40°-60°) gave the desired product (1.33 g), m.p. 146°-150° [α]D20 - 60.1° (c, 1.0, chloroform)

Workup

  1. temperatureThe mixture was heated to 60° for 2 hours
  2. customevaporated
  3. dissolutionthe residue dissolved in 1 N sodium bicarbonate solution (50 ml)
  4. washthe solution washed with ether
  5. additionExcess solid citric acid was added
  6. extractionthe product extracted into ethyl acetate
  7. dry with materialthe combined extracts dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-5b069f5b73304035ac72262a2c554839
Source dataset
uspto-grants-1977_11
Patent number
US04060603

Reaction notes

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