Triethylamine → HCID 86740264, compound

HRID 280775Notes

Reaction equation

HRID 280775 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.C(=O)(O)[O-].[Na+]>[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

7

Reactant 3

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

Product 1

HCID 86740264HCID 86740264, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

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 solution was distilled under reduced pressure leaving a residue. 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 solution was distilled under reduced pressure
  3. customleaving a residue
  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-f56578d37d4c4bb5b47c56cbb5ab502e
Source dataset
uspto-grants-1986_05
Patent number
US04590178

Reaction notes

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