Acetic Anhydride → (S)-4-(((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)-2-nitrophenyl Acetate

HRID 509416Notes

Reaction equation

HRID 509416 reaction equation
[F:1][C:2]1[C:3]([C@H:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:32]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10](=[O:21])[NH:9][C@H:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=2)=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 71144294(S)-N-((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-4-hydroxy-3-nitrobenzamide

Product 1

HCID 86687996(S)-4-(((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)-2-nitrophenyl Acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-4-hydroxy-3-nitrobenzamide (83 mg, 0.191 mmol) and DCM (5 mL) were added acetic anhydride (0.2 mL, 2.120 mmol) and DIPEA (0.15 mL, 0.861 mmol). After stirring for 45 min, the reaction was quenched with water and after stirring for 3 days, the aqueous solution was filtered to give the title compound as a yellow solid. The resulting product was used in the next step without further purification. MS (ESI pos. ion) m/z: 478.1 (M+H).

Workup

  1. customthe reaction was quenched with water
  2. stirringafter stirring for 3 days
  3. filtrationthe aqueous solution was filtered

Sources & evidence

ORD record
ord-1ea1db74854d462998aaa631bb322b8c
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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