Acetic Anhydride → HCID 58619154, compound

HRID 1795696Notes

Reaction equation

HRID 1795696 reaction equation
C(OC(=O)C)(=O)C.[OH:8][C:9]1([CH3:41])[CH:21]([OH:22])[CH:20]=[CH:19][CH:18]([CH3:23])[CH:17](/[C:24](/[CH3:40])=[CH:25]/[CH:26]=[CH:27]/[CH:28]([CH3:39])[CH2:29][CH:30]2[O:38][CH:31]2[CH:32]([CH3:37])[CH:33]([OH:36])[CH2:34][CH3:35])[O:16][C:14](=[O:15])[CH:13]=[CH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl.O.C(OCC)(=O)C>[OH:8][C:9]1([CH3:41])[CH:21]([OH:22])[CH:20]=[CH:19][CH:18]([CH3:23])[CH:17](/[C:24](/[CH3:40])=[CH:25]/[CH:26]=[CH:27]/[CH:28]([CH3:39])[CH2:29][CH:30]2[O:38][CH:31]2[CH:32]([CH3:37])[CH:33]([OH:36])[CH2:34][CH3:35])[O:16][C:14](=[O:15])[CH:13]=[CH:12][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 7918Acetic Anhydride3×HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 86759975HCID 86759975, compound

Product 1

HCID 58619154HCID 58619154, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of acetic anhydride (0.74 mg, 7 μmol) in dichloromethane (0.1 mL) was added dropwise to a solution of (8E,12E,14E)-6,7,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-2,8,12,14-tetraen-11-olide (3.3 mg, 6.9 μmol), triethylamine (3.6 mg, 35 μmol) and dimethylaminopyridine (0.4 mg, 3.5 μmol) in dichloromethane (1 mL), followed by stirring at room temperature for 30 min. under nitrogen atmosphere. A solution of acetic anhydride (0.2 mg, 1.9 μmol) in dichloromethane (20 μL) was added dropwise thereto and the mixture was stirred at the same temperature for 30 min. Further, a dichloromethane solution (20 μL) of acetic anhydride (0.2 mg, 1.9 μmol) was added dropwise thereinto and the mixture was stirred at the same temperature for 30 min. Ethyl Acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane, 4:5) to obtain the title Compound B43-1 (0.8 mg, 21%) and Compound B43-2 (2.6 mg, 73%) as colorless oils, respectively.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 min
  2. stirringthe mixture was stirred at the same temperature for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane, 4:5)

Sources & evidence

ORD record
ord-9c4e10e7fd2f422b80128602c5a6dfbe
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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