Sulfuric Acid → HCID 69054584, compound

HRID 1787860Notes

Reaction equation

HRID 1787860 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[C:17]([NH:19][CH2:20][C:21](=O)[CH3:22])=[O:18])=[CH:11][CH:10]=1)[C:2]1C=CC=CC=1.S(=O)(=O)(O)[OH:36].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[O:34]=[C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32](=[O:33])[N:24]1[CH:16]([C:17]1[O:18][C:21]([CH3:22])=[CH:20][N:19]=1)[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:1](=[O:36])[CH3:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 69053466HCID 69053466, compound

Product 1

HCID 69054584HCID 69054584, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of 3-(4-Benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-(2-oxo-propyl)-propionamide (5) (220 mg, 0.5 mmol) in acetic anhydride (2 mL) at room temperature was added concentrated sulfuric acid (0.2 mL). The mixture was stirred at 55-60° C. for 2 h, then sodium acetate (200 mg) was added, and the mixture was concentrated in vacuo. To the residue was added cold water (10 mL), the precipitated solid was collected, washed with water and dried, and the product was purified by flash chromatography on silica gel (20% ethyl acetate in DCM) to afford acetic acid 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(5-methyl-oxazol-2-yl)-ethyl]-phenyl ester (110 mg, 56%) as a light yellow solid; 1H NMR (CDCl3): □7.80 (m, 2H), 7.70 (m, 2H), 7.25 (d, 2H), 6.95 (d, 2H), 6.7 (s, 1H), 5.7 (m, 1H), 3.8 (m, 2H), 2.26 (s, 3H), 2.21 (s, 3H); LCMS m/z 391.1 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionTo the residue was added cold water (10 mL)
  3. customthe precipitated solid was collected
  4. washwashed with water
  5. customdried
  6. customthe product was purified by flash chromatography on silica gel (20% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-d2f816afef8946e591b0b16b2214f1a5
Source dataset
uspto-grants-2009_03
Patent number
US07511063B2

Reaction notes

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