Hydrochloric Acid → HCID 25106869, compound

HRID 2423275Notes

Reaction equation

HRID 2423275 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32]C)=[O:31])=[CH:25][C:24]=2[O:34][CH3:35])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:36])[NH:17]2)(=[O:11])=[O:10].[OH-].[Li+].Cl>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=2[O:34][CH3:35])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:36])[NH:17]2)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59864884HCID 59864884, compound

Product 1

HCID 25106869HCID 25106869, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a room temperature solution of 1.4 (1.00 g, 1.82 mmol) dissolved in a mixture of methanol (5 mL) and water (5 mL) was added lithium hydroxide (190 mg, 7.90 mmol). The reaction mixture was stirred at room temperature for 1 h then poured into aqueous 1N hydrochloric acid solution. The aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed twice with water then brine, stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a yellow solid. The product was isolated by semi-preparative reversed phase HPLC to afford a colorless solid. LC-MS ESI (neg.) m/z: 533.0 (M−H). 1H NMR (400 MHz) (d6-DMSO) δ 12.30 (br s, 1H); 10.95 (s, 1H); 9.73 (s, 1H); 7.63 (d, J=8.4 Hz, 1H); 7.52 (d, J=2 Hz, 1H); 7.30 (dd, J=2.0 & 8.5 Hz, 1H); 7.09 (d, J=8.6 Hz, 1H); 6.87 (d, J=1.4 Hz, 1H); 6.57 (d, J=8.3 Hz, 1H); 6.31 (d, J=8.6 Hz, 1H); 6.22 (d, J=8.0 Hz, 1H); 6.13 (s, 1H); 3.69 (s, 3H); 3.50 (s, 2H); 2.37 (s, 3H) ppm.

Workup

  1. extractionThe aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed twice with water
  3. stirringbrine, stirred over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  6. customto afford a yellow solid
  7. customThe product was isolated by semi-preparative reversed phase HPLC
  8. customto afford a colorless solid

Sources & evidence

ORD record
ord-38c75ccd13734f03a2b8b6b022df66b6
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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