Diethylamine → HCID 21023994, compound

HRID 1795685Notes

Reaction equation

HRID 1795685 reaction equation
[C:1]([O:4][CH:5]1[C:6]([OH:60])([CH3:59])CCC(C(OC2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:46])=[CH:20]/[CH:21]=[CH:22]/[CH:23]([CH3:45])[CH2:24][CH:25]2[O:44][CH:26]2[CH:27]([CH3:43])C(C(OC2C=CC([N+]([O-])=O)=CC=2)=O)CC)[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].[CH2:61]([NH:63][CH2:64][CH3:65])[CH3:62]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:4][CH:5]1[C:6]([OH:60])([CH3:59])[CH2:16][CH2:17][CH:5]([O:4][C:1](=[O:3])[N:63]([CH2:64][CH3:65])[CH2:61][CH3:62])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:46])=[CH:20]/[CH:21]=[CH:22]/[CH:23]([CH3:45])[CH2:24][CH:25]2[O:44][CH:26]2[CH:27]([CH3:43])[CH:14]([O:13][C:11](=[O:12])[N:63]([CH2:64][CH3:65])[CH2:61][CH3:62])[CH2:15][CH3:18])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 21024030HCID 21024030, compound

Product 1

HCID 21023994HCID 21023994, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(8E,12E,14E)-7-Acetoxy-6-hydroxy-6,10,12,16,20-pentamethyl-3,21-di(4-nitro-phenylcarboxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (12.6 mg) was dissolved in tetrahydrofuran (0.5 mL), and diethylamine (20 μL) was added thereto, followed by stirring for 21.0 hours. The reaction solution was diluted with ethyl acetate (20 mL), and washed with purified water (4 mL) twice and brine (4 mL). The resulting organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated. The resulting crude product was purified by thin layer chromatography (MERCK Silicagel 60 F254, 0.5 mm, developing solution; ethyl acetate) to obtain the title compound (10.7 mg, 14.5 μmol, 100.0%) as a colorless oil.

Workup

  1. washwashed with purified water (4 mL) twice
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product was purified by thin layer chromatography (MERCK Silicagel 60 F254, 0.5 mm, developing solution; ethyl acetate)

Sources & evidence

ORD record
ord-e0a41f3caf494e1aa03a096e8b0da7b7
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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