Lithium Hydroxide → HCID 67270028, compound

HRID 1039669Notes

Reaction equation

HRID 1039669 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:13][C:14]1[CH:22]=[C:21]([F:23])[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[C:9]([O:11]C)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][C:14]1[CH:22]=[C:21]([F:23])[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[C:9]([OH:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 67269606HCID 67269606, compound

Product 1

HCID 67270028HCID 67270028, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonyl)-3-(7-fluorobenzo[d][1,3]dioxol-5-yl)propanoate (12000 mg, 35 mmol) in 200 mL of THF at 0° C. was added LiOH (0.2 M) (52735 μl, 52735 μmol) dropwise over 10 minutes. After stirring for 1 hour, more LiOH (0.2 M) (17578 μl, 17578 mmol) was added and the mixture was stirred for another 1 hr. The reaction mixture was washed with ether (2×250 mL), the aqueous layer was acidified with 2N HCl to pH of about 4 and extracted with EtOAc (3×300 mL). The combined organics were washed with water, brine, dried over sodium sulfate, filtered and concentrated to provide (S)-2-(tert-butoxycarbonyl)-3-(7-fluorobenzo[d][1,3]dioxol-5-yl)propanoic acid (11.3 g, 98% yield) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for another 1 hr
  2. washThe reaction mixture was washed with ether (2×250 mL)
  3. extractionextracted with EtOAc (3×300 mL)
  4. washThe combined organics were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3220186e59c048fb8dc23821260898f0
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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