Dicyclohexylcarbodiimide → HCID 21024012, compound

HRID 1446628Notes

Reaction equation

HRID 1446628 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([OH:7])=[O:6])[CH3:2].[C:8]([O:11][CH:12]1[C:13]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:14][CH2:15][CH:16](O)[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])[CH3:9].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>ClCCl.C(OCC)(=O)C>[C:8]([O:11][CH:12]1[C:13]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:14][CH2:15][CH:16]([O:6][C:5](=[O:7])[CH2:4][O:3][CH2:1][CH3:2])[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])[CH3:9]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12301Ethoxyacetic acidHCID 218852-DimethylaminopyridineHCID 21024022HCID 21024022, compound

Product 1

HCID 21024012HCID 21024012, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethoxyacetic acid (8.2 mg, 0.079 mmol) in dichloromethane (1.6 mL) was added to (8E,12E,14E)-7-acetoxy-6,21-di(1-ethoxyethoxy)-3-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (13 mg, 0.016 mmol) at room temperature, and dicyclohexylcarbodiimide (20 mg, 0.094 mmol) and dimethylaminopyridine (1.9 mg, 0.016 mmol) were further added at room temperature. The mixture was stirred at room temperature for 6 hours. The reaction solution was diluted with ethyl acetate, and filtered through Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=70:30) to obtain the title compound (11 mg, 91%) as a colorless oil. ESI-MS m/z 789 (M+Na)+.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=70:30)

Sources & evidence

ORD record
ord-edc91fe340a640feb3425f4d584185e0
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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