Sodium Hydroxide → HCID 69103339, compound

HRID 2220431Notes

Reaction equation

HRID 2220431 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=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]([CH2:27][CH:28]([CH3:30])[CH3:29])[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]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([CH2:27][CH:28]([CH3:29])[CH3:30])[CH:18]=2)=[CH:15][CH:16]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69103505HCID 69103505, compound

Product 1

HCID 69103339HCID 69103339, compoundYield 76.6%

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-isobutyl-4-biphenylcarboxylate (390 mg) in methanol (3.90 ml) and tetrahydrofuran (1.56 ml) was added 1N aqueous sodium hydroxide solution (2.20 ml) and the mixture was stirred at room temperature for 2 days. Methanol and tetrahydrofuran were removed by evaporation under reduced pressure and to the mixture was added ethyl acetate (20 ml). The pH was adjusted to 4.3 with 1N hydrochloric acid and the organic layer was separated, washed with water (20 ml) and brine (20 ml) and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/2) to give 4′-[2-[[tert-butoxycarbonyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-ethyl]-3-isobutyl-4-biphenylcarboxylic acid (291 mg) as a white solid (foam).

Workup

  1. customMethanol and tetrahydrofuran were removed by evaporation under reduced pressure and to the mixture
  2. additionwas added ethyl acetate (20 ml)
  3. customthe organic layer was separated
  4. washwashed with water (20 ml) and brine (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation under reduced pressure
  8. customgave a crude product which
  9. customwas purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-5d7011e553534a758cae6a7427c3031d
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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