Lithium hydroxide, monohydrate → 3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid

HRID 220891Notes

Reaction equation

HRID 220891 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3[CH:24]=[CH:25][CH:26]=[CH:27][C:18]2=3)=[O:16])=[CH:11][CH:10]=1>O.O1CCOCC1>[N:17]1([C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][C:6]([OH:28])=[O:5])=[CH:14][CH:13]=2)=[O:16])[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2[CH:24]=[CH:25][CH:26]=[CH:27][C:18]1=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575553603-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid Methyl Ester

Product 1

HCID 575553343-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic AcidYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (114 mg, 2.72 mmol) was added to a solution of 3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic acid methyl ester from Example E65.3 (415 mg, 1.23 mmol) in water (5 ml) and dioxan (20 ml). The mixture was stirred for 18 h at room temperature then concentrated in vacuo. The residue was dissolved in chloroform, washed with 1M HCl solution then brine, dried and concentrated in vacuo to yield the title compound (241 mg, 61%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with 1M HCl solution
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ce41a267ada44b6bf4c650b27d8eb6c
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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