Dicyclohexylcarbodiimide → HCID 21024016, compound

HRID 1446630Notes

Reaction equation

HRID 1446630 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([OH:7])=[O:6])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[C:32]([O:35][CH:36]1[C:37]([OH:76])([CH3:75])[CH2:38][CH2:39][CH:40]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:41][C:42]([O:44][CH:45](/[C:50](/[CH3:66])=[CH:51]/[CH:52]=[CH:53]/[CH:54]([CH3:65])[CH2:55][CH:56]2[O:64][CH:57]2[CH:58]([CH3:63])[CH:59](O)[CH2:60][CH3:61])[CH:46]([CH3:49])[CH:47]=[CH:48]1)=[O:43])(=[O:34])[CH3:33]>ClCCl.C(OCC)(=O)C>[C:32]([O:35][CH:36]1[C:37]([OH:76])([CH3:75])[CH2:38][CH2:39][CH:40]([O:67][Si:68]([C:71]([CH3:72])([CH3:73])[CH3:74])([CH3:69])[CH3:70])[CH2:41][C:42]([O:44][CH:45](/[C:50](/[CH3:66])=[CH:51]/[CH:52]=[CH:53]/[CH:54]([CH3:65])[CH2:55][CH:56]2[O:64][CH:57]2[CH:58]([CH3:63])[CH:59]([O:6][C:5](=[O:7])[CH2:4][O:3][CH2:1][CH3:2])[CH2:60][CH3:61])[CH:46]([CH3:49])[CH:47]=[CH:48]1)=[O:43])(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12301Ethoxyacetic acidHCID 218852-DimethylaminopyridineHCID 21024018HCID 21024018, compound

Product 1

HCID 21024016HCID 21024016, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethoxyacetic acid (23 mg, 0.22 mmol), dicyclohexylcarbodiimide (55 mg, 0.27 mmol) and dimethylaminopyridine (5.4 mg, 0.27 mmol) were added to a solution of (8E,12E,14E)-7-acetoxy-3-t-butyldimethylsiloxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (29 mg, 0.044 mmol) in dichloromethane (3 mL) at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction mixture 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 (28 mg, 85%) as a colorless oil.

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-907bc5aa623b44008aa9b003c784a336
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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