Sulfuric Acid → HCID 178441290, compound

HRID 1888641Notes

Reaction equation

HRID 1888641 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:22])[C:12]1[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:13]=1[O:20][CH3:21])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)[OH:28].C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:1]([C:5]1=[CH:6][N:7]([C:23]([CH3:25])([CH3:24])[CH3:26])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:22])[C:12]1[CH:17]=[C:16]([CH:15]=[CH:14][C:13]=1[O:20][CH3:21])[C:18]([NH2:19])=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 178441289HCID 178441289, compound

Product 1

HCID 178441290HCID 178441290, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

The product from Example 26E (110 mg, 0.3 mmol) was treated with concentrated sulfuric acid (1 mL). The mixture was heated at 40° C. for 1 hr, diluted with H2O, neutralized with saturated Na2CO3, and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 107 mg (93%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 0.99 (t, J=7.32 Hz, 3 H) 1.40-1.48 (m, 2 H) 1.66 (s, 9 H) 1.69-1.76 (m, 2 H) 2.84 (dd, J=7.63 Hz, 2 H) 3.99 (s, 3 H) 7.06 (d, J=8.54 Hz, 1 H) 7.96 (s, 1 H) 8.02 (dd, J=8.85, 2.44 Hz, 1 H) 8.51 (d, J=2.44 Hz, 1 H); MS (DCI/NH4+) m/z 390 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0ee0525f28a14178841d09f7f9afd57d
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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