Water → CC-17369

HRID 2277131Notes

Reaction equation

HRID 2277131 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[C:11]([OH:22])[CH:12]=[CH:13][C:14]=3[NH:18]C(=O)[O-])[C:9]2=[O:23])[CH2:6][CH2:5][C:4](=[O:24])[NH:3]1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[NH2:18][C:14]1[CH:13]=[CH:12][C:11]([OH:22])=[C:10]2[C:15]=1[C:16](=[O:17])[N:8]([CH:7]1[CH2:6][CH2:5][C:4](=[O:24])[NH:3][C:2]1=[O:1])[C:9]2=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 178526077HCID 178526077, compound

Product 1

HCID 86709849CC-17369Yield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,6-dioxopiperidin-3-yl)-7-hydroxy-1,3-dioxoisoindolin-4-ylcarbamate C3-4 (6.73 g, 17.2 mmol) in DCM (200 mL) was added TFA (20 mL) slowly. The mixture was stirred at room temperature overnight. Water (20 mL) was added to quench the reaction. The mixture was extracted with EA (100 mL×3). The combined organic layers were collected and dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography (silica gel, DCM:MeOH:PE) to give 4-amino-2-(2,6-dioxopiperidin-3-yl)-7-hydroxyisoindoline-1,3-dione 3 as a yellow solid (4.05 g, yield: 81%). 1H NMR (DMSOd6, 400 MHz) δ: 1.95-1.98 (m, 1H), 2.52-2.58 (m, 2H), 2.83-2.92 (m, 1H), 4.98 (dd, J=12.6, 5.4 Hz, 1H), 6.06 (s, 2H), 6.95 (d, J=8.8 Hz, 1H), 7.06 (d, J=9.2 Hz, 1H), 10.17 (s, 1H), 11.05 (s, 1H); MS (ESI+): m/z 290 (M+1); Elem. Anal. Calcd. for C13H11N3O5: C, 53.98; H, 3.83; N, 14.53. Found C, 53.96; H, 3.74; N, 14.45.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EA (100 mL×3)
  4. customThe combined organic layers were collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel, DCM:MeOH:PE)

Sources & evidence

ORD record
ord-e4bcdf3f54e5434abb061b223a422d4a
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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