Dicyclohexylcarbodiimide → HCID 21024016, compound

HRID 1795680Notes

Reaction equation

HRID 1795680 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-f3606830fb214448af20ee5b60d731ed
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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