Sodium Hydroxide → HCID 67097419, compound

HRID 2078634Notes

Reaction equation

HRID 2078634 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:35][C@H:36]([OH:43])[C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19]([O:27][CH:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:35][C@H:36]([OH:43])[C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([O:27][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67097384HCID 67097384, compound

Product 1

HCID 67097419HCID 67097419, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-(cycloheptyloxy)-4-biphenylcarboxylate (813 mg) in methanol (8.1 ml) and tetrahydrofuran (2.4 ml) was added 1N sodium hydroxide (4.14 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was quenched by the addition of 1N hydrochloric acid (4.14 ml) and the solvent was removed by evaporation. The residue was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-(cycloheptyloxy)-4-biphenylcarboxylic acid (575 mg) as a white solid.

Workup

  1. customThe mixture was quenched by the addition of 1N hydrochloric acid (4.14 ml)
  2. customthe solvent was removed by evaporation
  3. customThe residue was chromatographed on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ba51f96ec4b24aa9b09baf85428f34d9
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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