Ethylmorpholine → Boc-MePhe methioninol

HRID 443922

Reaktionsgleichung

Reaktionsgleichung von HRID 443922
[C:1]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1CCOCC1)C.C(OC(Cl)=O)C(C)C.[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42]>O1CCCC1.C(O)(=O)C>[C:1]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2].[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42]

Komponenten

7

Edukt 4

HCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 2724404L-MethioninolHCID 7010602Boc-N-Me-Phe-OH

Produkt 1

HCID 131712176Boc-MePhe methioninol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3.1 g of Boc-MePhe-OH are dissolved in 30 ml of tetrahydrofuran, cooled to -20°, and 1.45 ml of N-ethylmorpholine are added with stirring followed by 1.45 ml of chloroformic acid iso-butyl ester and the mixture stirred for a further 5 minutes at -20°. A cold solution of 1.80 g of methioninol in 1 ml of tetrahydrofuran is added, the mixture left to stand for 2 hours at a temperature of from -5° to 0° and then stirred for 2 hours at room temperature. The reaction mixture is diluted with ca. 350 ml of acetic acid and washed repeatedly with water, 1 N citric acid, 10% KHCO3 and 30% NaCl solution. The organic phase is dried over Na2SO4 and evaporated, whereby Boc-MePhe-methioninol is obtained as an amorphous product.

Aufarbeitung

  1. temperaturecooled to -20°
  2. stirringthe mixture stirred for a further 5 minutes at -20°
  3. waitthe mixture left
  4. stirringstirred for 2 hours at room temperature
  5. washwashed repeatedly with water, 1 N citric acid, 10% KHCO3 and 30% NaCl solution
  6. dry with materialThe organic phase is dried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a177efbe882b49f99b0a5f2d55b737f4
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04261888

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