Hydrochloric Acid → (2R)-3-(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)-2-hydroxypropanoic acid

HRID 561234Notes

Reaction equation

HRID 561234 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][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]4[O:26]C(C)(C)[O:24][C:23]4=[O:29])[O:18][N:17]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[K+].Cl>CO>[Br:1][C:2]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][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]([OH:26])[C:23]([OH:29])=[O:24])[O:18][N:17]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66696815(5R)-5-[(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-one

Product 1

HCID 59738185(2R)-3-(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)-2-hydroxypropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (5R)-5-[(3-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-one (200 mg, 0.36 mmol) in MeOH (5 mL) was added KOH (61 mg, 1.08 mmol). The resulted solution was stirred at rt overnight, adjusted to pH 1 with HCl solution (1 mol/L), and then extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude product was purified by preparative HPLC 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. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e32d3914d3914289a973278f698009eb
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

Loading…