Ethyl Acetate → HCID 57215774, compound

HRID 487833Notes

Reaction equation

HRID 487833 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH:15](C)[C:16]2(C)O[SiH3])[C:11](=[O:46])[O:10][CH:9]([C:47]([CH3:61])=[CH:48][CH:49]2[CH2:54][CH2:53][CH:52]([NH:55][C:56](=[O:58])[CH3:57])[CH:51]([O:59][CH3:60])[CH2:50]2)[CH:8]([CH3:62])[CH:7](C(C)(C)C)[CH2:6][C:5]1=[O:67])[CH:2]=[CH2:3].F.C(OCC)(=[O:71])C>C(#N)C>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:46])[O:10][CH:9]([C:47]([CH3:61])=[CH:48][CH:49]2[CH2:54][CH2:53][CH:52]([NH:55][C:56](=[O:58])[CH3:57])[CH:51]([O:59][CH3:60])[CH2:50]2)[CH:8]([CH3:62])[CH:7]([OH:71])[CH2:6][C:5]1=[O:67])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14917Hydrofluoric AcidHCID 131718366HCID 131718366, compound

Product 1

HCID 57215774HCID 57215774, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A portion of the product from step (a) (13 mg) was dissolved in acetonitrile (4 ml) and to this was added 40% aqueous hydrofluoric acid (0.1 ml). After stirring for 2 hours at room temperature the reaction mixture was poured into ethyl acetate and the separated organic extract was then washed with water, saturated aqueous sodium hydrogen carbonate solution and brine before being dried (MgSO4), filtered and evaporated to an oil in vacuo. Column chromatography on silica eluting with hexane/acetone [2:1] then gave the title compound (8 mg) as a foam.

Workup

  1. extractionthe separated organic extract
  2. washwas then washed with water, saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to an oil in vacuo

Sources & evidence

ORD record
ord-55401d1ee2694558a3dff2fb9132abcf
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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