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

HRID 1713017Notes

Reaction equation

HRID 1713017 reaction equation
C([O:3][C:4](=[O:32])[CH:5](CC)[CH2:6][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>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([C:14]2[O:15][C:16]3[CH:17]=[C:10]4[C:9](=[O:29])[N:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:32])=[O:3])[C:27](=[S:28])[N:11]4[C:12]=3[CH:13]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 962Water2×HCID 86618327ethyl 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 115095444-[2-(4-nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyric acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

Compound 1 (10 mg, 0.023 mmol) was dissolved in trifluoroacetic acid (TFA, 2 ml), to give a clear red solution. Water (0.5 ml) was added and the mixture was heated at 70° C. overnight. Additional water (2 ml) was then added and the solvents of the reaction mixture were evaporated to give Compound 2 as a yellow-brown solid (8.5 mg, 88% yield).

Workup

  1. customto give a clear red solution
  2. customthe solvents of the reaction mixture were evaporated

Sources & evidence

ORD record
ord-47e4579d93db49b5b93ec4240e225f13
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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