Acetone → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 4422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4422
[NH:1]([C:17]([O:19]C(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].C(N([CH2:29][CH3:30])CC)C.C(OC(ON=[C:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:44]#N)=O)C1C=CC=CC=1.C(O[CH2:56][CH3:57])(=O)C.[CH3:58][C:59]([CH3:61])=O>O>[NH:1]([C:17]([CH2:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:46][CH2:43][CH2:44][CH2:56][CH2:57][CH2:29][CH3:30])=[O:19])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:59]1[CH:61]=[CH:4][CH:2]=[CH:3][CH:58]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3]

Komponenten

7

Edukt 5

HCID 180Acetone2×HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 540061222-Benzyloxycarbonyloxyimino-2-phenylacetonitrileHCID 131713573Boc-L-Ala-D-Glu(OH)OMe

Produkt 1

HCID 131713574stearoyl-L-Ala-D-Glu(OH)OBzlAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-mesoDAP-(L)-GlyOH (1) (1.2 g) in water (5 ml) was added triethylamine (0.96 g) and a solution of benzyloxycarbonyloxyimino-2-phenylacetonitrile (0.69 g) in acetone (5 ml) at 0° C. with stirring and the mixture was stirring over night at room temperature. After evapolation of acetone to the residue was added water (5 ml) and ethyl acetate (5 ml). The aqueous layer was separated, washed with ethyl acetate (5 ml), acidified with 1N-hydrochloric acid, and extracted with ethyl acetate (20 ml). The extract was washed with water (5 ml×2) and dried over magnesium sulfate. Evaporation of the solvent gave 1.42 g (94.7%) of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-Z-(D)-mesoDAP-(L)-GlyOH (2). ##STR551##

Aufarbeitung

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate (5 ml)
  3. extractionextracted with ethyl acetate (20 ml)
  4. washThe extract was washed with water (5 ml×2)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-cb80480d56a947c299041233295b2f80
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725582

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