Triethylamine → HCID 86740264, compound

HRID 485580Notes

Reaction equation

HRID 485580 reaction equation
[NH2:1][C@H:2]([C:8]([N:10]1[CH2:24][CH2:23][CH2:22][C@H:11]1[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.[CH2:37]([P:44](Cl)([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C.O>[CH2:46]([P:44]([NH:1][C@H:2]([C:8]([N:10]1[CH2:24][CH2:23][CH2:22][C@H:11]1[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7])([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:45])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 17747291HCID 17747291, compoundHCID 86740265HCID 86740265, compound

Product 1

HCID 86740264HCID 86740264, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

The thus obtained amorphous L-glutamyl-L-prolyl-L-proline was dissolved in DMF (8 ml) and water (2 ml), and neutralized by addition of triethylamine (0.2 ml) while cooling to -5° C. Dibenzylphosphorylchloride carbon tetrachloride solution (3 m mole) and triethylamine were added dropwise to the mixture while keeping the temperature to not more than 5° C. and usually keeping the pH value to 8-9. The mixture was stirred for 3 hours at room temperature, and the solvent was distilled off under reduced pressure. The residue was dissolved in 5% sodium bicarbonate and then washed with ethyl acetate. The aqueous phase was acidified with 1N hydrochloric acid, and the desired product was extracted with ethyl acetate. The ethyl acetate phase was washed with sodium chloride solution and dried with anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure. The residue was re-precipitated with ethyl acetate-ethyl ether to obtain dibenzylphosphoryl-L-glutamyl-L-prolyl-L-proline (140 mg).

Workup

  1. customto not more than 5° C.
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 5% sodium bicarbonate
  4. washwashed with ethyl acetate
  5. extractionthe desired product was extracted with ethyl acetate
  6. washThe ethyl acetate phase was washed with sodium chloride solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationThe ethyl acetate was distilled off under reduced pressure
  9. customThe residue was re-precipitated with ethyl acetate-ethyl ether

Sources & evidence

ORD record
ord-76b867715987464ab8a4463d01516b2e
Source dataset
uspto-grants-1985_08
Patent number
US04536395

Reaction notes

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