Tetrahydrofuran → HCID 66617793, compound

HRID 559391Notes

Reaction equation

HRID 559391 reaction equation
O[Li].O.[C:4]([O:8][C:9]([C@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=1)[C:12]([O:14]C)=[O:13])=[O:10])([CH3:7])([CH3:6])[CH3:5].C1COCC1>O>[C:4]([O:8][C:9]([C@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=1)[C:12]([OH:14])=[O:13])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66618233(R)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)propanoate

Product 1

HCID 66617793HCID 66617793, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

LiOH—H2O (0.6246 g, 14.88 mmol) was added to a solution of (R)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)propanoate (1.646 g, 4.961 mmol) in 1:1 THF:H2O (26 mL). The reaction mixture was stirred at room temperature for 2 hours, after which it was diluted with H2O and washed with EtOAc. The aqueous layer was then acidified with solid KHSO4 and extracted with DCM. The combined extracts were dried (Na2SO4), filtered, concentrated, and then re-concentrated from DCM/hexanes to give (R)-2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)-propanoic acid (1.31 g, 83.10% yield) as a white powder. LCMS (APCI) m/z 316 [M−H]−.

Workup

  1. washwashed with EtOAc
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationre-concentrated from DCM/hexanes

Sources & evidence

ORD record
ord-1d7c81b858d14cfa830570524ac913d5
Source dataset
uspto-grants-2011_11
Patent number
US08063050B2

Reaction notes

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