Acetic Acid → (4-{4-(Ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetic acid

HRID 913179Notes

Reaction equation

HRID 913179 reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][C:15]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=12)[CH3:2].C(O)(=O)C.Cl>O>[CH2:1]([O:3][C:4]1[C:12]2[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][C:30]([F:31])([F:33])[F:32])=[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=12)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58012494Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate

Product 1

HCID 24760117(4-{4-(Ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate (0.119 g, 0.23 mmol) was heated to 100° C. in a 1:1 mixture of acetic acid:2N aqueous hydrochloric acid (10 ml) for 2 hours. On addition of water, the resulting cream solid was collected by filtration and washed with water. This was purified by MDAP to give the title compound as a white solid (0.073 g, 0.15 mmol). LC/MS: Rt=3.38, [MH]+ 492.

Workup

  1. filtrationthe resulting cream solid was collected by filtration
  2. washwashed with water
  3. customThis was purified by MDAP

Sources & evidence

ORD record
ord-660000c3d2f44a2fab5b9185928659b4
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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