Diisopropyl Ether → HCID 58124898, compound

HRID 1971702Notes

Reaction equation

HRID 1971702 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16]([N:18]([CH3:31])[C:19]([CH3:30])([CH2:21][CH2:22][C:23]#[C:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[CH3:20])=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:33][CH3:34].C([O-])(=O)C.[Na+].[NH4+].[OH-].C(OC(C)C)(C)C>C(OC(=O)C)(=O)C.O>[CH3:31][N:18]1[C:19]([CH3:20])([CH3:30])[CH2:21][CH2:22][C:23]2[C:24]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[C:9]3[C:10]4[CH:11]=[C:2]([Br:1])[C:3]([O:33][CH3:34])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]3[C:15]=2[C:16]1=[O:17]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 66919870HCID 66919870, compound

Product 1

HCID 58124898HCID 58124898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
102.5 °C

Procedure

A mixture of 100 mg of 12j and 150 mg of anhydrous sodium acetate in 4 ml of acetic anhydride was heated at 100-105° C. for 2 h. The mixture was cooled and diluted with 10 ml of water and stirred at ambient temperature for 1 hr in order to decompose excess anhydride. The reaction mixture was neutralized by addition of cold conc. aq. NH4OH and then extracted with ethyl acetate. The extract was washed twice with water, dried, concentrated and the residue was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate. The purified product thus isolated was treated with diisopropyl ether, to give 65 mg of crystalline 12k; Mp 173-175° C.; Rf 0.45 (heptane/ethyl acetate 1/1). MS-ESI: [M+1] 484.96, 586.98.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed twice with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography over silica gel
  7. customThe purified product thus isolated

Sources & evidence

ORD record
ord-7819acaa703043f7b9efeb3c28abebde
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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