Acetic Acid → HCID 44439215, compound

HRID 1364548Notes

Reaction equation

HRID 1364548 reaction equation
[C:1]1([S:7][C:8]2[CH:29]=[CH:28][C:11]([CH2:12][NH:13][C:14]([C:16]3[CH:21]=[C:20]([NH2:22])[C:19]([C:23]#[N:24])=[C:18]([O:25][CH2:26][CH3:27])[N:17]=3)=[O:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=[O:32])C.OO.O>CN(C)C=O>[C:1]1([S:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:14]([C:16]3[CH:21]=[C:20]([NH2:22])[C:19]([C:23]#[N:24])=[C:18]([O:25][CH2:26][CH3:27])[N:17]=3)=[O:15])=[CH:28][CH:29]=2)=[O:32])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 66920728HCID 66920728, compound

Product 1

HCID 44439215HCID 44439215, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 161B (61 mg, 0.15 mmol), 2 mL of acetic acid, 0.15 mL of hydrogen peroxide (30% solution in water) in 0.5 mL of N,N-dimethylformamide was stirred at room temperature for 2 h. Water was added, the resulting precipitate was then filtered. The solid was triturated with methanol to provide the titled compound as a beige solid (44 mg, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.1 Hz, 3H), 4.43-4.53 (m, 4H), 7.05 (s, 1H), 7.29 (bs, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.46-7.55 (m, 3H), 7.63-7.72 (m, 4H), 9.08 (t, J=6.4 Hz, 1H). MS (ESI+) m/e=421 (M+H)+.

Workup

  1. filtrationthe resulting precipitate was then filtered
  2. customThe solid was triturated with methanol

Sources & evidence

ORD record
ord-a03325db29c94f0f9962ce36b2c78621
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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