Hydrochloric Acid → HCID 67002734, compound

HRID 2362669Notes

Reaction equation

HRID 2362669 reaction equation
[Cl:1][C:2]1[C:3]([C:36]2[S:40][C:39]([C:41]3([O:45]COC)[CH2:44][CH2:43][CH2:42]3)=[N:38][CH:37]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16]([C:20](=[O:25])[CH2:21][N:22]([CH3:24])[CH3:23])[CH2:15][CH2:14]4)[N:8]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]([C:36]2[S:40][C:39]([C:41]3([OH:45])[CH2:44][CH2:43][CH2:42]3)=[N:38][CH:37]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16]([C:20](=[O:25])[CH2:21][N:22]([CH3:23])[CH3:24])[CH2:15][CH2:14]4)[N:8]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:27])=[O:28])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67003865HCID 67003865, compound

Product 1

HCID 67002734HCID 67002734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of Example 52C (0.083 g, 0.118 mmol) in tetrahydrofuran (0.8 mL) was treated with 10% aqueous HCl solution (0.25 mL), and the reaction was heated at 65° C. for 4 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound. MS ESI(+) m/z 662.2 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with additional ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e4280b1fdd6480eb02d55bb2e45fd1f
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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