Trifluoroacetic anhydride → HCID 10268021, compound

HRID 1369170Notes

Reaction equation

HRID 1369170 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@H:11]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[C:12]([OH:14])=O)=[CH:6][CH:5]=1)[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]2[C:7]([CH2:10][C@H:11]([N:15]3[C:23](=[O:24])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]3=[O:25])[C:12]2=[O:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 12040690HCID 12040690, compound

Product 1

HCID 10268021HCID 10268021, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(αS)-α-[(4-Ethoxyphenyl)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid (XIV, EXAMPLE 14, 13.6 g, 40 mmol) is suspended in methylene chloride (40 mL). Trifluoroacetic anhydride (11.4 mL, 80 mmol) is added over 20 min at 20-25°. The resulting mixture is added dropwise to a solution of ferric chloride (6.81 g, 42 mmol) in methylene chloride (80 mL) over 1 hr. After the reaction is complete, it is quenched with water (80 mL). The organic layer is separated and concentrated. The residue is purified with a by column chromatography (silica gel; ethyl acetate/hexane, 20/80) to give the title compound, NMR δ7.85, 7.73, 7.38, 7.26, 5.10, 4.07, 3.52, 3.30 and 1.43; CMR δ200.0, 167.4, 159.0, 143.5, 135.9, 134.1, 132.0, 127.3, 125.3, 123.5, 106.2, 63.9, 54.2, 31.2 and 14.6; HRMS (FAB) calculated for C19H15NO4 [M+1]=322.1079, found=322.1085.

Workup

  1. customit is quenched with water (80 mL)
  2. customThe organic layer is separated
  3. concentrationconcentrated
  4. customThe residue is purified with a by column chromatography (silica gel; ethyl acetate/hexane, 20/80)

Sources & evidence

ORD record
ord-05e30a3ca15946fea707801132b34cf0
Source dataset
uspto-grants-2003_06
Patent number
US06576769B2

Reaction notes

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