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

HRID 720956노트

반응식

HRID 720956 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-80655e5fe50041dcb93e915923ad6ca4
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135502B1

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