Pyridine → HCID 14988929, compound

HRID 481331Notes

Reaction equation

HRID 481331 reaction equation
[CH:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:18][CH2:17][C:14]3([O:16][CH2:15]3)[CH:13]([C:19]3([CH3:25])[CH:21]([CH2:22][CH2:23][OH:24])[O:20]3)[CH:12]2[O:26][CH3:27])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:28](OC(=O)C)(=[O:30])[CH3:29].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)C>[C:28]([O:24][CH2:23][CH2:22][CH:21]1[O:20][C:19]1([CH:13]1[CH:12]([O:26][CH3:27])[CH:11]([O:10][C:8](=[O:9])[NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:18][CH2:17][C:14]21[O:16][CH2:15]2)[CH3:25])(=[O:30])[CH3:29]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14988917HCID 14988917, compound

Product 1

HCID 14988929HCID 14988929, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-cyclohexylcarbamoyloxy-4-[3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2,5]-octane (5 mg), acetic anhydride (12 μl), pyridine (11 μl), and 4-dimethylaminopyridine (1 mg) in dichloromethane (1 ml) was stirred for 1.1 hours at ambient temperature. The mixture was diluted with diethyl ether and washed with brine (4×). The organic layer was dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel to yield 4-[3-(2-acetoxyethyl)-2-methyloxiranyl]-6-cyclohexylcarbamoyloxy-5-methoxy-1-oxaspiro[2,5]octane as an oil (3.7 mg).

Workup

  1. washwashed with brine (4×)
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-02e107afdcb9430cbeb0d2c5279f59f5
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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