HCID 22405886, compound → HCID 22148988, compound

HRID 2269577Notes

Reaction equation

HRID 2269577 reaction equation
O[CH2:2][C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[S:5][C:4]=1[C:25]([OH:27])=[O:26]>C(Cl)Cl>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:6]2[S:5][C:4]3[C:25](=[O:27])[O:26][CH2:2][C:3]=3[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][CH:9]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 22405886HCID 22405886, compound

Product 1

HCID 22148988HCID 22148988, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 110 mg of the product of Step 7 in 15 mL of CH2Cl2 was added 110 mg of 1-(3-dimethylamninopropyl)-3-ethyl-carbodiimide hydrochloride. After stirring for 20 min, the reaction was quenched with 20 mL of sat. NaHCO3 and extracted with 50 mL of EtOAc. The extract was dried over MgSO4 and concentrated in vacuo. The crude product was suspended in 10 mL of 2:1 EtOAc/hexane with vigorously stirring for 2 h, and filtered to provide 75 mg of the title product as a white solid.

Workup

  1. customthe reaction was quenched with 20 mL of sat. NaHCO3
  2. extractionextracted with 50 mL of EtOAc
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. stirringwith vigorously stirring for 2 h
  6. filtrationfiltered

Sources & evidence

ORD record
ord-264b32162c844728b5f909acac85dce0
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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