Water → 3,3-Dimethyl-4-[2-(4-nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyric acid

HRID 1713023Notes

Reaction equation

HRID 1713023 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]([CH3:31])([CH3:30])[CH2:7][N:8]1[C:27](=[S:28])[N:11]2[C:12]3[CH:13]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=4)[O:15][C:16]=3[CH:17]=[C:10]2[C:9]1=[O:29])C.O>FC(F)(F)C(O)=O>[CH3:30][C:6]([CH3:31])([CH2:7][N:8]1[C:27](=[S:28])[N:11]2[C:12]3[CH:13]=[C:14]([C:18]4[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=4)[O:15][C:16]=3[CH:17]=[C:10]2[C:9]1=[O:29])[CH2:5][C:4]([OH:32])=[O:3]

Participants

4

Reactant 2

HCID 962WaterHCID 115253303,3-dimethyl-4-[2-(4-nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyric acid ethyl ester

Product 1

HCID 116618623,3-Dimethyl-4-[2-(4-nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyric acidYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
90 °C

Procedure

Compound 7 (300 mg, 0.66 mmol) was dissolved in trifluoroacetic acid (TFA, 9 ml). Water (3 ml) was added and the resulting mixture was heated at 90° C. for 16 hours. The reaction mixture was then filtered, washed with ethanol and the solvents were evaporated under reduced pressure to give Compound 8 (234 mg, 83% yield) as an orange solid.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washwashed with ethanol
  3. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-4724c8be81bc45429ee7658f930f7239
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

Loading…