Triethylamine → N-(Benzyloxycarbonyl)-4,6-dibromotryptophan ethyl ester

HRID 2379120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379120
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[CH:14][C:15]=2[Br:17])[NH:10][CH:9]=1)[NH2:6])[CH3:2].C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[CH:14][C:15]=2[Br:17])[NH:10][CH:9]=1)[NH:6][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 186560674,6-Dibromotryptophan ethyl ester

Produkt 1

HCID 53945469N-(Benzyloxycarbonyl)-4,6-dibromotryptophan ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Mix DL-4,6-dibromotryptophan ethyl ester (1.20g, 3.07mmol), triethylamine (341mg, 3.38mmol)and methylene chloride (50mL). Add benzyl chloroformate (692mg, 4.06mmol) and stir for 12 hours. Dilute with methylene chloride, wash with 1M hydrochloric acid (100mL) and brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound.

Aufarbeitung

  1. washwash with 1M hydrochloric acid (100mL) and brine (100mL)
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. custompurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a024dcab52fc4279a4cbfe105bd69594
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360814

Notizen zur Reaktion

Wird geladen…