Sulfuric Acid → Fmoc-Cys(Trt)-OMe

HRID 1522328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522328
[NH2:1][C@H:2]([C:24]([O:26][CH3:27])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N([C:54]([O:56][CH2:57][CH:58]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:64]2[C:59]1=[CH:60][CH:61]=[CH:62][CH:63]=2)=[O:55])[C@H](C(O)=O)CSC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.S(=O)(=O)(O)O>CO>[NH:1]([C:54]([O:56][CH2:57][CH:58]1[C:59]2[C:64](=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:65]2[C:70]1=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:55])[C@H:2]([C:24]([O:26][CH3:27])=[O:25])[CH2:3][S:4][C:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 10429690(R)-methyl 2-amino-3-(tritylthio)propanoate

Produkt 1

HCID 59278482Fmoc-Cys(Trt)-OMe

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

and H2N-Cys(Trt)-OMe 26. 7.2 g (12.3 mmol) of Fmoc-Cys(Trt)-OH was dissolved in 70 ml of MeOH and added 1.5 ml of conc. sulfuric acid. The reaction mixture was refluxed for 4 hr, the solvent was removed. The mixture was then mixed with ethyl acetate, and washed with water, saturated NaHCO3, and brine. Removing the solvent under vacuum gave 25 as a white foamy solid. The crude product was dissolved in 20 ml of 20% piperidine solution in DMF. After 2 hr, the solvent was removed. Silicagel chromatography (CH2Cl2: MeOH=10:1) gave 4.0 g (86% two step yield) of 26 as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 hr
  2. customthe solvent was removed
  3. additionThe mixture was then mixed with ethyl acetate
  4. washwashed with water, saturated NaHCO3, and brine
  5. customRemoving the solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-822abfe420794c72b45c76758fcbcca1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09074300B2

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