4-Methylmorpholine → 2-Hydroxy-2,4-dimethyl-3-pentanone

HRID 330125

Reaktionsgleichung

Reaktionsgleichung von HRID 330125
C(C(C(=O)O)[C@@H](C(N[C@@H](C(O)=O)C)=O)NC(OCC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.CN1CCOCC1.ClC(OCC)=O.N[CH:46]([CH:51]([CH3:53])[CH3:52])[C:47]([OH:50])([CH3:49])[CH3:48]>OP(O)=O.O[Mo](O)(=O)=O.C(OCC)(=O)C.CCCCCC.O1CCCC1>[OH:50][C:47]([CH3:49])([C:46](=[O:12])[CH:51]([CH3:53])[CH3:52])[CH3:48]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 132479483-Amino-2,4-dimethylpentan-2-olHCID 53966575N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-alanine

Produkt 1

HCID 5477352-Hydroxy-2,4-dimethyl-3-pentanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acidKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a solution of 2.14 g. (5.0 mmole) beta-benzyl-N-benzyloxycarbonyl-L-aspartyl-D-alanine in 35 ml. tetrahydrofuran cooled to -15° was added 0.55 ml. (5.0 mmole) N-methylmorpholine and 0.48 ml. (5.0 mmole) ethyl chloroformate. The mixture was stirred at -15° to -10° C. for two minutes and 0.66 g. (5.0 mmole) 3-amino-2-hydroxy-2,4-dimethylpentane was added. The mixture was allowed to warm to room temperature, stirred overnight and worked-up as described in Example 5, Part B, to obtain the diprotected dipeptide amide, Rf 0.27 (TLC, ethyl acetate/hexane, 1:1, phosphomolybdic acid spray, heat) which was used directly in the next step.

Aufarbeitung

  1. additionwas added 0.55 ml
  2. stirringstirred overnight
  3. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-079a054ae14c446cae2a98d5a52d1fe9
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894464

Verknüpfte Notizen

Wird geladen…