Hydrochloric Acid → HCID 67003647, compound

HRID 2362657Notes

Reaction equation

HRID 2362657 reaction equation
[Cl:1][C:2]1[C:3]([C:38]2[S:42][C:41]([C:43]3([O:47]COC)[CH2:46][CH2:45][CH2:44]3)=[N:40][CH:39]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:20]=[C:19]4[C:14]([CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18]4)=[CH:13][CH:12]=3)[N:8]([S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:5]2=[N:6][CH:7]=1.Cl>CO>[Cl:1][C:2]1[C:3]([C:38]2[S:42][C:41]([C:43]3([OH:47])[CH2:46][CH2:45][CH2:44]3)=[N:40][CH:39]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:20]=[C:19]4[C:14]([CH2:15][CH2:16][NH:17][CH2:18]4)=[CH:13][CH:12]=3)[N:8]([S:28]([C:31]3[CH:32]=[CH:33][C:34]([CH3:35])=[CH:36][CH:37]=3)(=[O:29])=[O:30])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67003447HCID 67003447, compound

Product 1

HCID 67003647HCID 67003647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of Example 45A (0.09 g, 0.122 mmol) in methanol (0.7 mL) was treated with 10% aqueous HCl solution (0.165 mL), and the reaction was heated at 65° C. for 3 hours. The reaction was cooled to ambient temperature and concentrated. The concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound. ESI(+) m/z 591.1 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. customThe concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-60c2c3b9c4e94211b79d07fa5c405168
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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