Acetic Acid → 17Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-phenyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

HRID 2082626노트

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HRID 2082626 반응식
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6]([OH:56])[CH2:5][C:4]1=[O:57])[CH3:2].C(O)(=O)C.C(O)(=O)C.[C:66]1([Bi](C2C=CC=CC=2)C2C=CC=CC=2)[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.C(O)(=O)C.C(=O)(O)O.C1([Bi](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:7]([CH3:55])[CH:6]([OH:56])[CH2:5][C:4]1=[O:57])[CH3:2]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 3521348Acetic acid;triphenylbismuthaneHCID 50919509Triphenyl bismuth carbonateHCID 5702442717-Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13, 19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9]octacos-18-ene2,3,10,16-tetraone

생성물 1

HCID 5707651417Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-phenyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a stirred solution of 17-ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone (100 mg, 0.126 mmol, 1 eq) and Cu(OAc)2 (2.8 mg, 0.014 mmol, 0.11 eq) in CH2Cl2 (1 ml) in a 16 mL screw-cap vial equipped with a magnetic stir-bar is added triphenyl bismuth diacetate [prepared immediately prior to use by addition of acetic acid (0.030 mL, 0.504 mmol, 4 eq) to a suspension of triphenyl bismuth carbonate (127 mg, 0.253 mmol, 2 eq) in CH2Cl2 (1 ml)]. The reaction vessel is capped and the mixture stirred for five days. The reaction mixture is diluted with several milliliters of saturated aqueous NaHCO3 and extracted 4 times with CH2Cl2. The organic extracts are combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The product is isolated by preparative TLC on silica gel to give the title compound.

후처리

  1. customequipped with a magnetic stir-bar
  2. customprepared immediately
  3. customThe reaction vessel is capped
  4. extractionextracted 4 times with CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product is isolated by preparative TLC on silica gel

출처 및 근거

ORD 기록
ord-a7e56572aae04ee3a504ccc7eb409047
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05189042

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