tert-Butanol → HCID 57723489, compound

HRID 1436971Notes

Reaction equation

HRID 1436971 reaction equation
C(OC([O:6][CH:7]1[CH2:19][CH2:18][C:17]([O:21]C(OCC)C)([CH3:20])[CH:16]([O:27][C:28]([N:30]2[CH2:35][CH2:34][CH:33]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:32][CH2:31]2)=[O:29])[CH:15]=[CH:14][CH:13]([CH3:41])[CH:12](/[C:42](/[CH3:69])=[CH:43]/[CH:44]=[CH:45]/[C:46]([O:63]C(OCC)C)([CH3:62])[CH2:47][CH:48]2[O:61][CH:49]2[CH:50]([CH3:60])[CH:51]([O:54]C(OCC)C)[CH2:52][CH3:53])[O:11][C:9](=[O:10])[CH2:8]1)C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(O)(C)C>O1CCCC1>[OH:6][CH:7]1[CH2:19][CH2:18][C:17]([OH:21])([CH3:20])[CH:16]([O:27][C:28]([N:30]2[CH2:31][CH2:32][CH:33]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:34][CH2:35]2)=[O:29])[CH:15]=[CH:14][CH:13]([CH3:41])[CH:12](/[C:42](/[CH3:69])=[CH:43]/[CH:44]=[CH:45]/[C:46]([OH:63])([CH3:62])[CH2:47][CH:48]2[O:61][CH:49]2[CH:50]([CH3:60])[CH:51]([OH:54])[CH2:52][CH3:53])[O:11][C:9](=[O:10])[CH2:8]1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 86602609HCID 86602609, compound

Product 1

HCID 57723489HCID 57723489, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the crude product of (8E,12E,14E)-3,6,16,21-tetrakis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-7-((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)oxy-18,19-epoxytricosa-8,12,14-trien-11-olide (11 mg, 11 μmol) was added a solution of pyridinium p-toluenesulfonate (11.4 mg, 45 μmol) in a mixture of tetrahydrofuran:2-methyl-2-propanol=1:1 (1 mL) at room temperature. To the mixture was added molecular sieves 4 Å (10 mg), followed by stirring at room temperature for 18.5 hours. Additional pyridinium p-toluenesulfonate (11.4 mg, 45 μmol) was added, followed by stirring at room temperature for 72 hours. The reaction mixture was evaporated, and the resulting residue was diluted with ethyl acetate, and then washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtrated and evaporated. The resulting residue was purified by thin layer chromatography (Fuji Silysia, NH Silica gel Plate, methanol:dichloromethane=1:19) to give the title compound (2.88 mg, 35%, two steps) as a colorless oil.

Workup

  1. customat room temperature
  2. additionTo the mixture was added molecular sieves 4 Å (10 mg)
  3. stirringby stirring at room temperature for 72 hours
  4. customThe reaction mixture was evaporated
  5. additionthe resulting residue was diluted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium bicarbonate and brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltrated
  9. customevaporated
  10. customThe resulting residue was purified by thin layer chromatography (Fuji Silysia, NH Silica gel Plate, methanol:dichloromethane=1:19)

Sources & evidence

ORD record
ord-b9434a3f683f4b4582cafdcecc202e79
Source dataset
uspto-grants-2009_11
Patent number
US07619100B2

Reaction notes

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