Tetrahydrofuran → HCID 66617793, compound

HRID 532727Notes

Reaction equation

HRID 532727 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-f2c88b6e74ea41c6a888c2dd5f9bdca8
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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