Isopropanol → m-Chloroperbenzoic acid

HRID 371307

Reaktionsgleichung

Reaktionsgleichung von HRID 371307
[CH2:1]([Cl:3])Cl.CCC(C1O[C@]2(OC3CC=C(C)[C@@H](OC4O[C@@H](C)[C@H](OC5O[C@@H](C)[C@H](O)[C@@H](OC)C5)[C@@H](OC)C4)[C@@H](C)C=C[CH:26]=[C:27]4COC5[C@H](O)C(C)=[CH:33][CH:32]([C:38]([O:40][C@@H](C3)C2)=[O:39])[C@:31]45O)C=C[C@@H]1C)C.C([OH:69])(C)C.CCC([C@H]1O[C@]2(O[C@@H]3CC=C(C)[C@@H](O[C@@H]4O[C@@H](C)[C@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](OC)C5)[C@@H](OC)C4)[C@@H](C)C=CC=C4CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(O[C@@H](C3)C2)=O)[C@]45O)C=C[C@@H]1C)C>C1C=CC=CC=1>[Cl:3][C:1]1[CH:26]=[CH:27][CH:31]=[C:32]([C:38]([O:40][OH:69])=[O:39])[CH:33]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 6344Dichloromethane2×HCID 6858006AvermectinHCID 44372930(3S,4'S,6S,10'E,12'S,13'S,14'E,16'E,21'R,24'S)-2-butan-2-yl-21',24'-dihydroxy-12'-[(4S,5S,6S)-5-[(4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one

Produkt 1

HCID 70297m-Chloroperbenzoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of 4.7 mg of 85% metachloroperbenzoic acid and 0.5 ml of fresh methylene chloride is prepared, is placed in a test tube, fitted with a septum and immersed in a dry ice acetone bath. There was added a solution of 0.5 ml of methylene chloride containing 20 mg of avermectin B1a/B1b. The reaction mixture is stirred under nitrogen at -70° C. for two hours and at -30° C. for 30 minutes. Then the reaction mixture was placed in an ice bath for 4 hr. and in a refrigerator for 2 days. The reaction mixture was placed on an 8×8 inch chromatography plate with a layer of 250 microns of silica gel and developed with 5% isopropanol in benzene three times. Two fractions are observed: the faster moving fraction weighing 6.4 mg; a slower moving fraction weighing 8.2 mg. The mass spectral and nuclear magnetic resonance analysis of both fractions indicate that the slow moving fraction was avermectin B 1a/B1b-8,9-epoxide.

Aufarbeitung

  1. customis placed in a test tube
  2. customfitted with a septum
  3. customimmersed in a dry ice acetone bath
  4. waitThen the reaction mixture was placed in an ice bath for 4 hr
  5. waitand in a refrigerator for 2 days

Quellen und Nachweise

ORD-Eintrag
ord-8d6b91656cdc4304a1b97c49a0284936
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530921

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