Water → HCID 57875813, compound

HRID 1665645Notes

Reaction equation

HRID 1665645 reaction equation
O[Li].O.C([O:6][C:7](=[O:28])[CH2:8][C:9](=[O:27])[N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=2)[CH2:12][CH2:11]1)C.C1COCC1.O>CO>[O:27]=[C:9]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=2)[CH2:12][CH2:11]1)[CH2:8][C:7]([OH:28])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57875808HCID 57875808, compound

Product 1

HCID 57875813HCID 57875813, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (93 mg, 2.2 mmol) was added to a solution of 3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionic acid ethyl ester (400 mg, 1.1 mmol) in a mixture of methanol (2 mL), THF (5 mL) and H2O (2 mL). The resulting mixture was stirred for 2 hours at room temperature. The mixture was then concentrated and the residue was diluted with water, washed with diethyl ether and acidified with concentrated HCl. The residue was extracted with ethyl acetate and concentrated to afford 230 mg (62%) of 3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionic acid. LCMS: 331.09 (M+1)+, 90.2%, 1H NMR: (CDCl3): δ 7.0 (t, 2H), 3.7 (s, 4H), 3.5 (m, 6H).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionthe residue was diluted with water
  3. washwashed with diethyl ether
  4. extractionThe residue was extracted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9d4fb1e4bf34e538cfa0af23fdcfe6e
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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