Potassium Carbonate → HCID 131716250, compound

HRID 330052Notes

Reaction equation

HRID 330052 reaction equation
C(O[CH:5]1[CH2:31][C:30](=[O:32])[CH:29]([CH2:33][CH:34]=[CH2:35])[CH:28]=[C:27]([CH3:36])[CH2:26][CH:25]([CH3:37])[CH2:24][CH:23]([O:38][CH3:39])[CH:22]2[O:40][C:18]([OH:44])([CH:19]([CH3:43])[CH2:20][CH:21]2[O:41][CH3:42])[C:17](=[O:45])[C:16](=[O:46])[N:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:47])[O:8][CH:7]([C:48]([CH3:76])=[CH:49][C:50]2([O:62][SiH:63]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[CH2:55][CH2:54][CH:53]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH:52]([O:60][CH3:61])[CH2:51]2)[CH:6]1[CH3:77])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)C>[CH2:33]([CH:29]1[CH:28]=[C:27]([CH3:36])[CH2:26][CH:25]([CH3:37])[CH2:24][CH:23]([O:38][CH3:39])[CH:22]2[O:40][C:18]([OH:44])([CH:19]([CH3:43])[CH2:20][CH:21]2[O:41][CH3:42])[C:17](=[O:45])[C:16](=[O:46])[N:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:47])[O:8][CH:7]([C:48]([CH3:76])=[CH:49][C:50]2([O:62][SiH:63]([C:70]3[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=3)[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[CH2:55][CH2:54][CH:53]([C:56]([CH3:58])([CH3:59])[CH3:57])[CH:52]([O:60][CH3:61])[CH2:51]2)[CH:6]([CH3:77])[CH:5]=[CH:31][C:30]1=[O:32])[CH:34]=[CH2:35]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131716251HCID 131716251, compound

Product 1

HCID 131716250HCID 131716250, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 14-acetoxy-17-allyl-12-[2-(4-tertbutyl-diphenylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (43.8 mg) in tetrahydrofuran (1.5 ml) was added potassium carbonate (ca 100 mg) at room temperature and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was diluted with diethyl ether and the resulting solution was washed with a saturated aqueous ammonium chloride, water and an aqueous sodium chloride successively, and dried over sodium sulfate. The resulting solution was concentrated under reduced pressure and the residue was purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 3:2 v/v) to give 17-allyl-12-[2-(4-tertbutyl-diphenylsilyloxy-3-methoxycyclohexyl)-1methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacosa-14,18-diene-2,3,10,16-tetraone (30 mg).

Workup

  1. washthe resulting solution was washed with a saturated aqueous ammonium chloride, water
  2. dry with materialan aqueous sodium chloride successively, and dried over sodium sulfate
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. customthe residue was purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 3:2 v/v)

Sources & evidence

ORD record
ord-0ada0806112b45ecbf8e891dbe00d655
Source dataset
uspto-grants-1990_01
Patent number
US04894366

Reaction notes

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