HCID 66916713, compound → HCID 66916737, compound

HRID 37744Notes

Reaction equation

HRID 37744 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][N:8]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])(C)(C)C>C(O)=O>[O:26]([C:23]1[CH:22]=[CH:21][C:20]([S:17]([N:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]([OH:33])=[O:5])(=[O:19])=[O:18])=[CH:25][CH:24]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 66916713HCID 66916713, compound

Product 1

HCID 66916737HCID 66916737, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Compound 4a (1.02 g, 2.14 mmol) was dissolved in formic acid (10 mL) and stirred overnight at room temperature. The solid was filtered off, the filtrate was evaporated in vacuo, and co-evaporated with toluene (6×20 mL). The pure product obtained was dried overnight in high vacuum. Yield: 0.71 g, 1.95 mmol, 91% (off-white solid). 1H-NMR (DMSO-d6): δ 7.91 (d, 2H, 3JHH=9.0 Hz, ArH), 7.20 (d, 2H, 3JHH=9.0 Hz, ArH), 7.28 (d, 2H, 3JHH=9.0 Hz, ArH), 7.00 (d, 1H, 3JHH=9.0 Hz, ArH), 6.87 (d, 2H, 3JHH=9.0 Hz, ArH), 4.07 (s, 4H, 2×CH2CO2H).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe pure product obtained
  4. customwas dried overnight in high vacuum

Sources & evidence

ORD record
ord-a06dae072eb2430396e7a4c03ad82404
Source dataset
uspto-grants-2013_09
Patent number
US08524194B2

Reaction notes

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