Water → HCID 21023946, compound

HRID 1795690Notes

Reaction equation

HRID 1795690 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]([O:11][CH:12]1[C:13]([O:55][CH:56]([O:58][CH2:59][CH3:60])[CH3:57])([CH3:54])[CH2:14][CH2:15][CH:16]([O:48][CH:49]([O:51][CH2:52][CH3:53])[CH3:50])[CH2:17][C:18]([O:20][CH:21](/[C:26](/[CH3:47])=[CH:27]/[CH:28]=[CH:29]/[CH:30]([CH3:46])[CH2:31][CH:32]2[O:45][CH:33]2[CH:34]([CH3:44])[CH:35]([O:38][CH:39]([O:41][CH2:42][CH3:43])[CH3:40])[CH2:36][CH3:37])[CH:22]([CH3:25])[CH:23]=[CH:24]1)=[O:19])=[O:10].C(OCC)(=O)C.O>CN(C)C=O>[CH2:52]([O:51][CH:49]([O:48][CH:16]1[CH2:15][CH2:14][C:13]([O:55][CH:56]([O:58][CH2:59][CH3:60])[CH3:57])([CH3:54])[CH:12]([O:11][C:9](=[O:10])[CH2:8][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:24]=[CH:23][CH:22]([CH3:25])[CH:21](/[C:26](/[CH3:47])=[CH:27]/[CH:28]=[CH:29]/[CH:30]([CH3:46])[CH2:31][CH:32]2[O:45][CH:33]2[CH:34]([CH3:44])[CH:35]([O:38][CH:39]([O:41][CH2:42][CH3:43])[CH3:40])[CH2:36][CH3:37])[O:20][C:18](=[O:19])[CH2:17]1)[CH3:50])[CH3:53]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8857Ethyl AcetateHCID 21024035HCID 21024035, compound

Product 1

HCID 21023946HCID 21023946, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Morpholine (9 mg, 0.103 mmol) was added to a solution of (8E,12E,14E)-7-chloroacetoxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (8.1 mg, 10.3 μmol) in N,N-dimethylformamide (1 mL) at room temperature, followed by stirring at 60° C. for one hour. Ethyl Acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was washed with water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:2 and 1:1, successively) to obtain the title compound (7.3 mg, 85%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm

Sources & evidence

ORD record
ord-8243aa0b071b4014a6e395f014e90b75
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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