Acetic Anhydride → HCID 59444760, compound

HRID 1160591Notes

Reaction equation

HRID 1160591 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C:12](=[O:14])[CH3:13])(=O)[CH3:9].[OH:15][C@@H:16]1[CH2:27][CH2:26][C@:25]([OH:29])([CH3:28])[C@@H:24](O)[CH:23]=[CH:22][C@H:21]([CH3:31])[C@@H:20](/[C:32](/[CH3:36])=[CH:33]/C=C)[O:19][C:18](=[O:37])[CH2:17]1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.ClCCl>[C:12]([O:11][C@@H:8]1[C@@:25]([OH:29])([CH3:28])[CH2:26][CH2:27][C@@H:16]([OH:15])[CH2:17][C:18](=[O:37])[O:19][C@H:20](/[C:21](/[CH3:31])=[CH:22]/[CH:23]=[CH2:24])[C@@H:32]([CH3:36])[CH:33]=[CH:9]1)(=[O:14])[CH3:13]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59444764HCID 59444764, compound

Product 1

HCID 59444760HCID 59444760, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (35.6 μl, 246 μmol), acetic anhydride (11.6 μl, 123 μmol) and 4-dimethylaminopyridine (3.0 mg, 24.6 μmol) were added to an anhydrous dichloromethane (2 ml) solution of (4R,7R,8S,9E,11S,12S)-4,7,8-trihydroxy-7,11-dimethyl-12-[(1E)-1-methylbuta-1,3-dien-1-yl]-oxacyclododec-9-en-2-one (40.0 mg, 123 μmol) at 0° C. and the reaction solution was stirred at the same temperature for one hour. The reaction solution was poured into a saturated sodium hydrogen carbonate aqueous 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=1:2) to obtain the title compound (42 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=1:2)

Sources & evidence

ORD record
ord-6d01d1f6238943bfb7895c8ae1b8c9a8
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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