4-Methylmorpholine → N-t-butoxycarbonyl-L-tyrosyl-glycylglycyl-L-phenylalanyl-L-methionine sulfoxide

HRID 614205

Reaktionsgleichung

Reaktionsgleichung von HRID 614205
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:37]([OH:39])=O)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])=[O:23])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:55][C@H:56]([C:62]([OH:64])=[O:63])[CH2:57][CH2:58][S:59]([CH3:61])=[O:60]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:37]([NH:55][C@H:56]([C:62]([OH:64])=[O:63])[CH2:57][CH2:58][S:59]([CH3:61])=[O:60])=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])=[O:23])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 158980Methionine SulfoxideHCID 15689707N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine

Produkt 1

HCID 22807105N-t-butoxycarbonyl-L-tyrosyl-glycylglycyl-L-phenylalanyl-L-methionine sulfoxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

10.84 Parts N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine and 2.0 parts N-methylmorpholine are dissolved in 200 parts dimethylformamide and cooled to -15° C. Then, 2.9 parts isobutyl chloroformate is added dropwise over a thirty minute period while keeping the temperature between -15° C. to -10° C. After the addition is completed, a solution of 3.3 parts L-methionine sulfoxide in 15 parts dimethylformamide is slowly added. The mixture is stirred for a further thirty minutes at -15° C. and then warmed to room temperature and stirred thereat for an additional 2 hours. The product is isolated by diluting the reaction mixture with 10 volumes water and extracting with ethyl acetate. The ethyl acetate extracts are combined, dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure. The residue is purified by low-pressure chromatography to afford N-t-butoxycarbonyl-L-tyrosyl-glycylglycyl-L-phenylalanyl-L-methionine sulfoxide.

Aufarbeitung

  1. custombetween -15° C. to -10° C
  2. additionAfter the addition
  3. temperaturewarmed to room temperature
  4. stirringstirred
  5. customThe product is isolated
  6. extractionextracting with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residue is purified by low-pressure chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e84d01dcc5bb477a9e3f431693996d68
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04144228

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