4-Methylmorpholine → Z-Trp-Gly-OCH3

HRID 2295710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295710
CN1CCOCC1.[NH:8]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:9]([C:20](O)=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[NH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].CP(OP(CC)(C)=O)(CC)=O.C([O-])(O)=O.[Na+]>>[NH:8]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:9]([C:20]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

Komponenten

6

Edukt 5

HCID 79724-MethylmorpholineHCID 69221Glycine methyl esterHCID 101176benzyloxycarbonyl-L-tryptophanHCID 103894Phosphinic acid, P-ethyl-P-methyl-, P,P'-anhydrideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 1823118Z-Trp-Gly-OCH3

Versuchsvorschrift

At 0° C. there were added while stirring 6.5 ml of N-methyl morpholine to a mixture of 3.35 g (0.05 mol) of Z-Trp-OH and 1.25 g of H-Gly-OMe. Into the solution obtained there were added dropwise at the temperature specified, while stirring, 4 g of methylethylphosphinic acid anhydride. The mixture was allowed to stand at room temperature for 10 hours and the solvent was separated by distillation in vacuo at room temperature. The residue was taken up by a mixture of 25 ml of water and 70 ml of ethyl acetate, the ethyl acetate extract was separated and the aqueous solution was extracted twice using each time 10 ml of ethyl acetate. The combined ethyl acetate extracts were washed twice using each time 7 ml of water, a 5% potassium sulfate solution (until an acid reaction took place) and a saturated NaHCO3 solution until a slightly alkaline reaction took place. Upon drying over magnesium sulfate and clearing with active carbon, the solvent was largely separated by distillation in vacuo and the residue was digested with diisopropyl ether.

Aufarbeitung

  1. additionAt 0° C. there were added
  2. customInto the solution obtained there
  3. additionwere added dropwise at the temperature
  4. customthe solvent was separated by distillation in vacuo at room temperature
  5. additionThe residue was taken up by a mixture of 25 ml of water and 70 ml of ethyl acetate
  6. extractionthe ethyl acetate extract
  7. customwas separated
  8. extractionthe aqueous solution was extracted twice
  9. washThe combined ethyl acetate extracts were washed twice
  10. customa 5% potassium sulfate solution (until an acid reaction
  11. customuntil a slightly alkaline reaction
  12. dry with materialUpon drying over magnesium sulfate and clearing with active carbon
  13. customthe solvent was largely separated by distillation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c755dab1c6704b63863fbeeaac7be97c
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04426325

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