Imidazole → HCID 57253034, compound

HRID 1885433Notes

Reaction equation

HRID 1885433 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:52])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([OH:51])[CH2:45]2)[CH:7]([CH3:53])[CH:6]([O:54][Si:55]([CH:62]([CH3:64])[CH3:63])([CH:59]([CH3:61])[CH3:60])[CH:56]([CH3:58])[CH3:57])[CH2:5][C:4]1=[O:65])[CH3:2].CN(C)C=O.N1C=CN=C1.[Si:76](Cl)([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:78])[CH3:77]>O.C(Cl)Cl>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:52])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][Si:76]([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:78])[CH3:77])[CH2:45]2)[CH:7]([CH3:53])[CH:6]([O:54][Si:55]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:62]([CH3:64])[CH3:63])[CH2:5][C:4]1=[O:65])[CH3:2].[CH3:33][O:32][CH:24]1[CH:23]2[O:34][CH:19]([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH2:8][CH:7]([CH3:53])[CH2:6][CH2:5][C:4](=[O:65])[CH2:3][CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25]1.[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:52])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][Si:76]([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:78])[CH3:77])[CH:46]([OH:51])[CH2:45]2)[CH:7]([CH3:53])[CH:6]([O:54][Si:55]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:62]([CH3:64])[CH3:63])[CH2:5][C:4]1=[O:65])[CH3:2]

Participants

9

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 57258887HCID 57258887, compound

Product 3

HCID 54077611HCID 54077611, compoundHCID 57092099HCID 57092099, compoundHCID 57253034HCID 57253034, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 17-ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(3",4"-di-hydroxycyclohexyl)-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 (80.9 gm, 8.65 mmol) in mixture of dimethylformamide (60 ml) and methylene chloride (30 ml) and imidazole (1.77 g) under N2 atmosphere was treated with t-butyldimethylsilyl chloride 1.74 g 11.55 mol). After stirring at RT for 16 hrs, the reaction mixture was poured into water (600 ml) and resultant suspension was extracted with ether. The combined extracts were washed with water (5 times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed over SiO2. Elution with methylene chloride-ethyl ether (100:10) yielded 17-Ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(3"-t-butyldimethylsilyloxy-4"-hydroxycyclohexyl)-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 (1.71 g, 17%, rf=0.66), 17-ethyl-1-hydroxy-14-triisopropylsilyoxy-12-[2'-(3"-t-butyldimethylsilyl-4"-hydroxycyclohecyl)-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 (1.82 gm, rf=0.41) and 17-ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(3"-hydroxy-4"-t-butyldimethylsilyloxycyclohexyl)-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 (1.67 gm, rf=0.31).

Workup

  1. extractionwas extracted with ether
  2. washThe combined extracts were washed with water (5 times)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed over SiO2
  6. washElution with methylene chloride-ethyl ether (100:10)

Sources & evidence

ORD record
ord-9ccd3560670f4927bedb14d1d3fd0049
Source dataset
uspto-grants-1992_09
Patent number
US05143918

Reaction notes

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