Hydrochloric Acid → HCID 57461785, compound

HRID 1020341Notes

Reaction equation

HRID 1020341 reaction equation
O[Li].O.[O:4]=[C:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[O:11][C:12]([C:19]([O:21]CC)=[O:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1.Cl>C1COCC1.CO.O.CCOC(C)=O.O>[O:4]=[C:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[O:11][C:12]([C:19]([OH:21])=[O:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57461786HCID 57461786, compound

Product 1

HCID 57461785HCID 57461785, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 21892291Methanol tetrahydrofuran waterSolventHCID 22728543Water ethylacetateSolvent

Procedure

LiOH.H2O (0.096 g, 2.28 mmol) was added to a solution of ethyl 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxylate (A-30) (0.140 g, 0.48 mmol) in THF/CH3OH/H2O (2/2/0.5 mL) at RT followed by stirring overnight. The reaction mixture was diluted with EtOAc/H2O (25/25 mL) and neutralized with 2.5 mL of 1 M HCl. The organic phase was separated, dried over MgSO4, filtered, and concentrated. The residue was dried in vacuo to yield 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxylic acid (A-31) as a white solid (0.120 g, 95% yield). 1H NMR (500 MHz, CD3OD) δ 5.18 (br s, 1H), 3.41 (t, 2H, J=6.8 Hz), 2.42 (t, 2H, J=7.2 Hz), 1.93 (m, 2H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-3c86453349fa4bedb3bd9e1db5da344c
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

Loading…