Triethylamine → HCID 6993127, compound

HRID 1448863Notes

Reaction equation

HRID 1448863 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].Cl>O1CCCC1.C(Cl)(Cl)Cl>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:5]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 6993127HCID 6993127, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-Pro-OH (73.2 g, 340 mmol) and triethylamine (47.6 ml, 340 mmol) in tetrahydrofurane (300 ml), cooled to -10°, was added isobutyl chloroformate (44.5 ml, 340 mmol). After 15 min., a solution of H-Gly-OMe.HCl (42.7 g, 340 mmol) and triethylamine (47.6 ml, 340 mmol) in chloroform (300 ml) was added to the stirring solution. The mixture was stirred at 0° for 1 h and at room temperature for 24 h. The organic solvent was removed under reduced pressure and the residue, dissolved in ethyl acetate, was washed with 10% citric acid solution, 4% sodium bicarbonate solution, water and dried over anhydrous sodium sulfate. The solution was evaporated and the oily residue was crystallized on addition of petroleum ether; yield 71.8 g (84%), m.p. 70°-72° C., Rf1 0.70.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. dissolutionthe residue, dissolved in ethyl acetate
  3. washwas washed with 10% citric acid solution, 4% sodium bicarbonate solution, water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solution was evaporated
  6. customthe oily residue was crystallized on addition of petroleum ether

Sources & evidence

ORD record
ord-27ce4fe98cd84b4c8d0574286c8b4642
Source dataset
uspto-grants-1980_02
Patent number
US04187852

Reaction notes

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