Hydrochloric Acid → HCID 59738192, compound

HRID 561237Notes

Reaction equation

HRID 561237 reaction equation
[Br:1][C:2]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[S:15][C:14]([C:16]3[N:20]=[C:19]([CH2:21][C@@H:22]([C:30]([O:32]CC)=[O:31])[NH:23]C(=O)C(F)(F)F)[O:18][N:17]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+].Cl>CCO.O>[Br:1][C:2]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[S:15][C:14]([C:16]3[N:20]=[C:19]([CH2:21][C@@H:22]([C:30]([OH:32])=[O:31])[NH2:23])[O:18][N:17]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86620468HCID 86620468, compound

Product 1

HCID 59738192HCID 59738192, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of ethyl 3-(3-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)-N-(trifluoroacetyl)-L-alaninate (550 mg, 0.86 mmol) in EtOH (5 mL) and water (5 mL) was added NaOH (104 mg, 2.6 mmol) and the resulting solution was stirred at rt overnight. The solution was adjusted to pH 7 with HCl solution (1 mol/L), then extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude product was washed with petroleum ether/EtOAc to afford the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. washThe crude product was washed with petroleum ether/EtOAc

Sources & evidence

ORD record
ord-fc56b0f2038e45f69cfc2c9555ee02e9
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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