Methanol → HCID 59444764, compound

HRID 1160590Notes

Reaction equation

HRID 1160590 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CO.[Si]([O:27][C@H:28]1[CH2:39][C:38](=[O:40])[O:37][C@H:36](/[C:41](/[CH3:45])=[CH:42]/[CH:43]=[CH2:44])[C@@H:35]([CH3:46])[CH:34]=[CH:33][C@@H:32]2[O:47][C@H](C3C=CC=CC=3)[O:49][C@:31]2([CH3:56])[CH2:30][CH2:29]1)(C(C)(C)C)(C)C.O>C(OCC)(=O)C>[OH:27][C@@H:28]1[CH2:29][CH2:30][C@:31]([OH:49])([CH3:56])[C@@H:32]([OH:47])[CH:33]=[CH:34][C@H:35]([CH3:46])[C@@H:36](/[C:41](/[CH3:45])=[CH:42]/[CH:43]=[CH2:44])[O:37][C:38](=[O:40])[CH2:39]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59516396HCID 59516396, compound

Product 1

HCID 59444764HCID 59444764, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Pyridinium p-toluene sulfonate (68.2 mg, 271 μmol) was added to a methanol (1.22 ml) solution of (2S,3aS,4E,6S,7S,11R,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-6,13a-dimethyl-7-[(1E)-1-methylbuta-1,3-dien-1-yl]-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (36.0 mg, 0.07 mmol) and the reaction solution was stirred at room temperature for four days. Distilled water (1 ml) was added to the reaction solution, and the reaction solution was diluted with ethyl acetate and washed with distilled water and brine sequentially, and after dried over anhydrous sodium sulfate, the drying agent was filtered off and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=1:3) to obtain the title compound (18.3 mg) as a white solid.

Workup

  1. washwashed with distilled water and brine sequentially
  2. dry with materialafter dried over anhydrous sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=1:3)

Sources & evidence

ORD record
ord-b193cc674c144570b94a8ad3297a1988
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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