Water → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl hydrogen phosphate

HRID 720956

Reaktionsgleichung

Reaktionsgleichung von HRID 720956
CC(C)C(O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@H]([O:25][C:26]2[CH:27]=[CH:28][C:29]3[C:35]4[C:36]([O:44][CH3:45])=[C:37]([O:42][CH3:43])[C:38]([O:40][CH3:41])=[CH:39][C:34]=4[CH2:33][CH2:32][C@H:31]([NH:46][C:47](=[O:49])[CH3:48])[C:30]=3[CH:50]=2)[C@@H]1OC(=O)C(C)C)=O.[P:58](Cl)(Cl)([O:60][CH3:61])=[O:59].[OH2:64]>C1COCC1>[P:58]([OH:59])([O:60][CH3:61])([O:25][C:26]1[CH:27]=[CH:28][C:29]2[C:35]3[C:36]([O:44][CH3:45])=[C:37]([O:42][CH3:43])[C:38]([O:40][CH3:41])=[CH:39][C:34]=3[CH2:33][CH2:32][C@H:31]([NH:46][C:47](=[O:49])[CH3:48])[C:30]=2[CH:50]=1)=[O:64]

Komponenten

5

Edukt 3

HCID 962WaterHCID 69611Methyl dichlorophosphateHCID 69586443(2R,3R,4S,5R,6R)-2-[(5S)-5-(Acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl]oxy-3,5-bis(isobutyryloxy)-6-[(isobutyryloxy)methyl]tetrahydro-2H-pyran-4-yl 2-methylpropanoate

Produkt 1

HCID 58658627(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl hydrogen phosphateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel4×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of N-acetyl-colchicinol (1) (0.45 g; 1.26 mmol) in THF (40 ml) under argon was cooled to 0° C. and treated with a 1.0M solution of lithiumHMDS in THF (1.39 ml; 1.39 mmol). The mixture was stirred at 0° C. for 1 hour and then added in portions over about 15 minutes to a solution of methyl dichlorophosphate (625 μl; 4.16 mmol) in THF (150 ml). The mixture was stirred at ambient temperature for 15 minutes. After addition of water (200 ml) the THF was removed by evaporation. After removal of the insoluble material by filtration, the filtrate was purified on HP20 SS resin eluting with a gradient of 0–60% methanol/water. The appropriate fractions were freeze-dried to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl hydrogen phosphate as white solid (391 mg).

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 15 minutes
  2. customwas removed by evaporation
  3. customAfter removal of the insoluble material
  4. filtrationby filtration
  5. customthe filtrate was purified on HP20 SS resin
  6. washeluting with a gradient of 0–60% methanol/water
  7. customThe appropriate fractions were freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-80655e5fe50041dcb93e915923ad6ca4
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135502B1

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