Acetic Acid → Erythromycin Thiocyanate

HRID 1260153

Reaktionsgleichung

Reaktionsgleichung von HRID 1260153
CC(C)=O.C(O)(=O)C.[S-:9][C:10]#[N:11].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH3:19][CH2:20][C@H:21]1[O:36][C:34](=[O:35])[C@H:33]([CH3:37])[C@@H:32]([O:38][C@@H:39]2[O:44][C@@H:43]([CH3:45])[C@H:42]([OH:46])[C@@:41]([O:48][CH3:49])([CH3:47])[CH2:40]2)[C@H:31]([CH3:50])[C@@H:30]([O:51][C@@H:52]2[O:57][C@H:56]([CH3:58])[CH2:55][C@H:54]([N:59]([CH3:61])[CH3:60])[C@H:53]2[OH:62])[C@@:29]([OH:64])([CH3:63])[CH2:28][C@@H:27]([CH3:65])[C:25](=[O:26])[C@H:24]([CH3:66])[C@@H:23]([OH:67])[C@@:22]1([OH:69])[CH3:68]>C(OCCCC)(=O)C.O>[CH3:19][CH2:20][C@H:21]1[O:36][C:34](=[O:35])[C@H:33]([CH3:37])[C@@H:32]([O:38][C@@H:39]2[O:44][C@@H:43]([CH3:45])[C@H:42]([OH:46])[C@@:41]([O:48][CH3:49])([CH3:47])[CH2:40]2)[C@H:31]([CH3:50])[C@@H:30]([O:51][C@@H:52]2[O:57][C@H:56]([CH3:58])[CH2:55][C@H:54]([N:59]([CH3:60])[CH3:61])[C@H:53]2[OH:62])[C@@:29]([OH:64])([CH3:63])[CH2:28][C@@H:27]([CH3:65])[C:25](=[O:26])[C@H:24]([CH3:66])[C@@H:23]([OH:67])[C@@:22]1([OH:69])[CH3:68].[C:10]([SH:9])#[N:11]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 180AcetoneHCID 10340Sodium CarbonateHCID 12560Erythromycin4×HCID 516871Sodium thiocyanate

Produkt 1

HCID 83938Erythromycin Thiocyanate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel4×HCID 31272Butyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
37.5 °C

Versuchsvorschrift

In a three-necked flask, 12 g of erythromycin was dissolved in butyl acetate or acetone, added with 2M acetic acid aqueous solution and 10% sodium thiocyanate solution (in a molar ratio to erythromycin of 1:1:1-1.2), and stirred continuously at 15-60° C. After complete reaction, the mixture was added with water, cooled to a temperature between −25° C. and 10° C., filtered, the resultant solid was washed with water, filtered under a reduced pressure, and dried at 60° C. for about 4 h to obtain an off-white crystal powder. HPLC analysis: the main peak of the sample had a retention time in consistent with that of erythromycin control, in which the content of erythromycin was 88.46% (the theoretical value: 88.54%); melting point: 165.8-169.8° C. (not corrected), water content by Karl Fischer method was 4.62% (the theoretical value: 4.35%), TG-DTG: weight loss before 140° C. was about 4.51%, which was in the error range of the sample having 2 crystal water (see FIG. 6), MS (ESI, FAB) m/z: 793, 792, 734, 733, 59, 58. Element analysis: found: C, 54.93; H, 8.87; N, 3.29; S, 3.76; calculated: C, 55.05; H, 8.75; N, 3.38; S, 3.87. The obtained sample having 2 crystal water was added to a sodium carbonate solution to generate a precipitate, the precipitate was washed with water, recrystallized from water-ethanol, and the product was consistent with raw material erythromycin in terms of specific optical rotation and MS data.

Aufarbeitung

  1. customAfter complete reaction
  2. temperaturecooled to a temperature between −25° C. and 10° C.
  3. filtrationfiltered
  4. washthe resultant solid was washed with water
  5. filtrationfiltered under a reduced pressure
  6. customdried at 60° C. for about 4 h
  7. customto obtain an off-white crystal powder
  8. custombefore 140° C.
  9. washthe precipitate was washed with water
  10. customrecrystallized from water-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5ca4d11c6c6a479f8042cd188539e27b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470787B2

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