Lithium hydroxide, monohydrate → HCID 67517700, compound

HRID 2173297Notes

Reaction equation

HRID 2173297 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].O[Li].O>CO.C1COCC1.O>[C:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[O:12][CH2:11]2)[CH2:16][CH2:17]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67515763HCID 67515763, compound

Product 1

HCID 67517700HCID 67517700, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of tert-butyl 4-{[7-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-3-yl]methyl}piperazine-1-carboxylate (250 mg, 0.66 mmol) in 20 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (139 mg, 3.32 mmol), and the mixture was stirred at ambient temperature overnight. The solvents were removed under vacuum, and the residue was added 30 mL of water and extracted with ether. The aqueous layer was then acidified with 4 N HCl to pH=7 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was re-crystallized from DCM to give 3-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-2,3-dihydro-1-benzofuran-7-carboxylic acid.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 30 mL of water
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was re-crystallized from DCM

Sources & evidence

ORD record
ord-0dcff72c1ab74f8a9720bbe6a04511ac
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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