Sodium Hydroxide → HCID 86590693, compound

HRID 1823107Notes

Reaction equation

HRID 1823107 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:31][C@@H:32]([C:34]1[CH:35]=[N:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[OH:33])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]CC)=[O:25])=[CH:20][C:19]=2[O:29][CH3:30])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.C(OCC)(=O)C.Cl>[C:1]([O:5][C:6]([N:8]([CH2:31][C@@H:32]([C:34]1[CH:35]=[N:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[OH:33])[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][C:19]=2[O:29][CH3:30])=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86590694HCID 86590694, compound

Product 1

HCID 86590693HCID 86590693, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4′-[3-[(tert-butoxycarbonyl)-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-2-methoxy-1,1′-biphenyl-4-carboxylate in ethanol (5.0 ml) was added 1N sodium hydroxide (1.0 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1) to give 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-2-methoxy-1,1′-biphenyl-4-carboxylic acid (100 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-0974ad8bfb57433bbac0c3bd1f73bfd7
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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