HCID 59457665, compound → HCID 59457731, compound

HRID 1711096Notes

Reaction equation

HRID 1711096 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH:15]=3)[S:13][C:6]=12>C(Cl)Cl>[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH:15]=3)[S:13][C:6]=12

Participants

3

Reactant 1

HCID 59457665HCID 59457665, compound

Product 1

HCID 59457731HCID 59457731, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxylate 388 (1 g, 2.13 mmol) in DCM (4.3 mL) TFA (4.3 mL) was added and the reaction mixture was stirred 2 h at room temperature. The solvent was removed under reduced pressure, the residue was suspended in aqueous sodium bicarbonate, the mixture was extracted with DCM, EtOAc and DCM; the combined extracts were filtered and the recovered solids were collected and dried. The filtrate was dried over anhydrous Na2SO4, concentrated under reduced pressure and the residue was combined with the solid material obtained upon filtration, to afford 389 (806 mg, 100% yield) as a yellow solid. LCMS:(M+H) 372.1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe mixture was extracted with DCM, EtOAc and DCM
  3. filtrationthe combined extracts were filtered
  4. customthe recovered solids were collected
  5. customdried
  6. dry with materialThe filtrate was dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customobtained upon filtration

Sources & evidence

ORD record
ord-1db1c13ae1de406dbb8a411222b51d45
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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