Hydrochloric Acid → HCID 58869963, compound

HRID 1191705Notes

Reaction equation

HRID 1191705 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:32])[CH2:13][S:14][CH:15]2[C:19]([CH3:20])=[C:18]([CH3:21])[C:17](=[O:22])[N:16]2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[S:9][CH:10]=1)C.[Li+].[OH-].Cl>C1COCC1.O.CCOC(C)=O>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:16]2[C:17](=[O:22])[C:18]([CH3:21])=[C:19]([CH3:20])[CH:15]2[S:14][CH2:13][C:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:33])=[O:3])[N:7]=2)=[O:32])=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86612282HCID 86612282, compound

Product 1

HCID 58869963HCID 58869963, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 7 (100 mg, 0.2 mmol) was dissolved in 4 mL THF and cooled to 0° C. LiOH (56 mg, 0.8 mmol) in 4 mL water was added dropwise. The mixture was warmed to room temperature and stirred for 3 h. The mixture was cooled to 0° C. and diluted with 10 mL EtOAc. 2N aq HCl was added until the mixture reached pH1. The aqueous phase was washed with EtOAc. The combined organics were washed with water, dried (Na2SO4), filtered, and evaporated. Recrystallization fro ether/hexane provided the title compound as a tan powder (60 mg, 63%). 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=9 Hz, 2H), 6.81 (m, 3H), 5.02 (d, J=15 Hz, 1H), 4.55 (s, 1H), 4.15 (d, J=15 Hz, 1H), 3.77 (s, 3H), 3.72 (s, 2H), 3.11 (d, J=15 Hz, 1H), 2.96 (d, J=15 Hz, 1H), 1.89 (s, 3H), 1.76 (s, 3H). MS: m/z (MH+) 462.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. washThe aqueous phase was washed with EtOAc
  4. washThe combined organics were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystallization fro ether/hexane

Sources & evidence

ORD record
ord-59c40aaa6cad4dfaa957119b863fa6e3
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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