Hydrochloric Acid → Z-Tyr-Gly-Gly-Phe-OCH2CN

HRID 1196815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196815
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:47][C@H:48]([C:56]([O:58][CH2:59][C:60]#[N:61])=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.Cl>CN(C=O)C.C(OCC)(=O)C>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:47][C@H:48]([C:56]([O:58][CH2:59][C:60]#[N:61])=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 15024388Carbobenzoxy-tyrosyl-glycyl-glycineHCID 54189157Phenylalanine cyanomethyl ester

Produkt 1

HCID 14101107Z-Tyr-Gly-Gly-Phe-OCH2CNAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

300 mg (0.69 mmole) of Z-Tyr-Gly-Gly-OH was dissolved in 5 mL dry THR, and the temperature was lowered to -10° C. in a dry ice/ethylene glycol bath. One equivalent of N-methyl morpholine and 1 equivalent of isobutyl chloroformate was added with stirring. One equivalent of H-L-Phe-OCH2CN, HCl (166 mg), and 1 equivalent of N-methyl morpholine dissolved in 2 mL DMF was added and the solution stirred for 5 minutes. The reaction was allowed to come to room temperature, then diluted with six volumes of ethyl acetate. The ethyl acetate was washed with cold water (2x), 0.1 N HCl (3x), 0.2 M Na2CO3 (2x), water (2x) and concentrated brine (1x). The ethyl acetate as concentrated carefully under vacuum, and the residue was recrystallized from CH2Cl2 /hexanes to give 260 mg (62%) of Z-Tyr-Gly-Gly-Phe-OCH2CN. Amino acid analysis: tyr1.0, gly1.9, phe0.9.

Aufarbeitung

  1. customdry THR
  2. customthe temperature was lowered to -10° C. in a dry ice/ethylene glycol bath
  3. additionwas added
  4. stirringthe solution stirred for 5 minutes
  5. customto come to room temperature
  6. washThe ethyl acetate was washed with cold water (2x), 0.1 N HCl (3x), 0.2 M Na2CO3 (2x), water (2x) and concentrated brine (1x)
  7. concentrationThe ethyl acetate as concentrated carefully under vacuum
  8. customthe residue was recrystallized from CH2Cl2 /hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3c1b553a239b4656b3d3600e9126612d
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116741

Notizen zur Reaktion

Wird geladen…