Acetate → 2-(1,3-Dihydro-1-oxo-3-thioxo-2H-isoindol-2-yl)-pentanedioic acid

HRID 1009089Notes

Reaction equation

HRID 1009089 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[S:11])[N:3]1[CH:12]([CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[C:13]([O:15]C)=[O:14].CC([O-])=O.Cl>C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[S:11])[N:3]1[CH:12]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 175AcetateHCID 313Hydrochloric AcidHCID 11404450HCID 11404450, compound

Product 1

HCID 113698572-(1,3-Dihydro-1-oxo-3-thioxo-2H-isoindol-2-yl)-pentanedioic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 208 (350 mg, 1.09 mmol) was stirred with a 1:1 mixture of acetic acid glacial and conc. HCl in a 100° C. oil bath for 2.5 h. Ethyl acetate (100 mL) and ice water (30 mL) were added. The ethyl acetate layer was separated, washed with ice water, dried over Na2SO4 and concentrated. The resulting syrup was crystallized with ether to afford compound 211 as red crystals (253 mg, 79%); mp 157° C.; 1H NMR (DMSO-d6) δ 8.04-7.96 (m, 1H), 7.91-7.74 (m, 3H), 5.43 (dd, J=5.1 Hz, J=9.6 Hz, 1H), 2.42-2.33 (m, 2H), 2.30-2.26 (m, 2H); MS (DEI) m/z 293 (M); HRMS (DEI) calcd. for C13H11NO5S 293.0358 (M+). found 293.0363; Anal. (C13H11NO5S) H, N; C: calcd, 53.24. found, 53.88.

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with ice water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting syrup was crystallized with ether

Sources & evidence

ORD record
ord-2cc155e22fcc4b169e9faff47a79f57b
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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