Water → Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe

HRID 1383740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383740
[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH:20]([CH3:38])[C@H:21]([C:34]([O:36][CH3:37])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C.CC(C)N=C=NC(C)C.CCOCC>[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([N:20]([CH3:38])[C@H:21]([C:34]([O:36][CH3:37])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:31])[CH3:32])[CH:24]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

8

Edukt 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131722749N-Me-Tyr(3-tBu)-OMe

Produkt 1

HCID 131722748Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 12734DiisopropylcarbodiimideLösungsmittel

Versuchsvorschrift

To a solution of 3.25 g of Z-N-Me-Val-OH, 2.2 g of N-Me-Tyr(3-tBu)-OMe and 1.88 g of HOBT in DMF (30 ml), DIC (1.9 ml) was added under cooling with ice and the mixture was stirred at room temperature for 23 hours. Water was added to the reaction mixture and extraction was effected with ether. The extract was washed with saturated brine and the organic layer was dried with sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 100:10:1) to give Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe in the amount of 1.96 g (47%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. washThe extract was washed with saturated brine
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. washeluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-d7def5f59e1748acb24adfc0f6389594
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255285B1

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