Acetic Anhydride → HCID 52946850, compound

HRID 1363842Notes

Reaction equation

HRID 1363842 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[CH3:15][CH2:16][C@H:17]([OH:49])[C@H:18]([C@H:20]1[O:22][C@@H:21]1[CH2:23][C@@H:24](/[CH:26]=[CH:27]/[CH:28]=[C:29](/[C@H:31]1[O:43][C:41](=[O:42])[CH2:40][C@H:39]([OH:44])[CH2:38][CH2:37][C@:36]([OH:46])([CH3:45])[C@@H:35]([OH:47])[CH2:34][CH2:33][C@@H:32]1[CH3:48])\[CH3:30])[CH3:25])[CH3:19].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:15][CH2:16][C@H:17]([OH:49])[C@H:18]([C@H:20]1[O:22][C@@H:21]1[CH2:23][C@@H:24](/[CH:26]=[CH:27]/[CH:28]=[C:29](/[C@H:31]1[O:43][C:41](=[O:42])[CH2:40][C@H:39]([OH:44])[CH2:38][CH2:37][C@:36]([OH:46])([CH3:45])[C@@H:35]([O:47][C:8]([CH3:9])=[O:10])[CH2:34][CH2:33][C@@H:32]1[CH3:48])\[CH3:30])[CH3:25])[CH3:19]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 52941941HCID 52941941, compound

Product 1

HCID 52946850HCID 52946850, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (17.2 μl, 123 μmol), acetic anhydride (5.83 μl, 616 μmol) and 4-dimethylaminopyridine (1.50 mg, 12.3 μmol) were added to anhydrous dichloromethane (2.00 ml) solution of pladienolide A (30.5 mg, 61.6 μmol) under stirring at 0° C. After the reaction solution was stirred at 0° C. for one hour, it was poured into a saturated sodium hydrogen carbonate aqueous solution, which was then extracted with ethyl acetate. After the organic layer was washed with brine, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:acetone=3:1→2:1) to obtain the title compound (27.2 mg) as a colorless oil. This was obtained as a white amorphous by purifying by HPLC (Shiseido, commercial name CAPCELL PAK C18SG120; acetonitrile:water=45:55) followed by performing lyophilization.

Workup

  1. stirringAfter the reaction solution was stirred at 0° C. for one hour
  2. extractionwas then extracted with ethyl acetate
  3. washAfter the organic layer was washed with brine, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:acetone=3:1→2:1)

Sources & evidence

ORD record
ord-e97211f6179f45d4a32609e9e1121e32
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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