Triethylamine → HCID 21024035, compound

HRID 1795688Notes

Reaction equation

HRID 1795688 reaction equation
Cl[CH2:2][C:3]([O:5][C:6](=[O:9])[CH2:7][Cl:8])=O.CN(C1C=CC=CN=1)C.[CH2:19]([O:21][CH:22]([O:24][CH:25]1[CH2:37][CH2:36][C:35]([O:39][CH:40]([O:42][CH2:43][CH3:44])[CH3:41])(C)[CH:34](O)C=[CH:32][CH:31]([CH3:46])[CH:30](/[C:47](/[CH3:68])=[CH:48]/[CH:49]=[CH:50]/[CH:51]([CH3:67])[CH2:52][CH:53]2[O:66][CH:54]2[CH:55]([CH3:65])[CH:56]([O:59][CH:60]([O:62][CH2:63][CH3:64])[CH3:61])[CH2:57][CH3:58])[O:29][C:27](=[O:28])[CH2:26]1)[CH3:23])[CH3:20].C(N(CC)CC)C>ClCCl.O.C(OCC)(=O)C>[Cl:8][CH2:7][C:6]([O:5][CH:3]1[C:35]([O:39][CH:40]([O:42][CH2:43][CH3:44])[CH3:41])([CH3:34])[CH2:36][CH2:37][CH:25]([O:24][CH:22]([O:21][CH2:19][CH3:20])[CH3:23])[CH2:26][C:27]([O:29][CH:30](/[C:47](/[CH3:68])=[CH:48]/[CH:49]=[CH:50]/[CH:51]([CH3:67])[CH2:52][CH:53]2[O:66][CH:54]2[CH:55]([CH3:65])[CH:56]([O:59][CH:60]([O:62][CH2:63][CH3:64])[CH3:61])[CH2:57][CH3:58])[CH:31]([CH3:46])[CH:32]=[CH:2]1)=[O:28])=[O:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10946Chloroacetic anhydrideHCID 218852-DimethylaminopyridineHCID 21023947(8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

Product 1

HCID 21024035HCID 21024035, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of chloroacetic anhydride (21.5 mmol, 0.122 mmol) and dimethylaminopyridine (1.2 mg, 10 μmol) in dichloromethane (0.5 mL) were added to a solution of (8E,12E,14E)-3,6,21-tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (17.4 mg, 24.4 μmol) and triethylamine (25 mg, 0.244 mmol) in dichloromethane (2 mL) at room temperature, followed by stirring at the same temperature for one hour. Ethyl Acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate, 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=1:4) to obtain the declared compound (18.1 mg, 94%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm, ethyl acetate-hexane=1:4)

Sources & evidence

ORD record
ord-1dcc7d1ff2c74c0cb03c765046e83cd0
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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