Hydrochloric Acid → HCID 25106871, compound

HRID 2423281Notes

Reaction equation

HRID 2423281 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]CC)=[O:31])=[CH:25][C:24]=2[O:35][CH3:36])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:38])[N:17]2[CH3:37])(=[O:11])=[O:10].[OH-].[Li+].Cl>O1CCCC1.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:35][CH3:36])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:38])[N:17]2[CH3:37])(=[O:11])=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59864836HCID 59864836, compound

Product 1

HCID 25106871HCID 25106871, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 3.4 (25 mg, 0.043 mmol) dissolved in a mixture of tetrahydrofuran (2 mL) and methanol (1 mL) was added a solution of lithium hydroxide (50 mg, 2.1 mmol) dissolved in water (1 mL). The reaction 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 colorless solid. LC-MS ESI (neg.) m/z: 547.0 (M−H). 1H NMR (400 MHz) (d6-DMSO) δ 12.30 (br s, 1H); 9.80 (br s, 1H); 7.63 (d, J=8.8 Hz, 1H); 7.53 (d, J=2.0 Hz, 1H); 7.31 (dd, J=2.4 & 8.8 Hz, 1H); 7.22 (d, J=8.8 Hz, 1H); 6.89 (d, J=1.6 Hz, 1H); 6.59 (d, J=1.6 Hz, 1H); 6.39 (d, J=8.8 Hz, 1H); 6.23 (dd, J=3.6 & 3.6 Hz, 1H); 3.70 (s, 3H); 3.63 (s, 3H); 3.52 (s, 2H): 2.41 (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 colorless solid

Sources & evidence

ORD record
ord-216c56f39b0b4f4da45c582518647355
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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