Sodium Hydroxide → HCID 69102782, compound

HRID 2220428Notes

Reaction equation

HRID 2220428 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:32][C@H:33]([OH:40])[C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=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][CH2:28][CH:29]([CH3:31])[CH3:30])[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]([CH2:32][C@H:33]([OH:40])[C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=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][CH2:28][CH:29]([CH3:30])[CH3:31])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69103484HCID 69103484, compound

Product 1

HCID 69102782HCID 69102782, compoundYield 99.2%

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-isobutoxy-4-biphenylcarboxylate (511 mg) in methanol (5.11 ml) and tetrahydrofuran (1.53 ml) was added 1N sodium hydroxide (2.79 ml) and the mixture was stirred at room temperature for 36 hours. Methanol and tetrahydrofuran were removed by evaporation under reduced pressure and the pH was adjusted to 5.9 with 0.1N hydrochloric acid. The mixture was extracted with ethyl acetate (twice) and the extract was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 4′-[2-[[tert-butoxycarbonyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-isobutoxy-4-biphenylcarboxylic acid (494 mg) as a brown solid (foam).

Workup

  1. customMethanol and tetrahydrofuran were removed by evaporation under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate (twice) and the extract
  3. washwas washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6827222eb4594aebb77f7c2479b6e61b
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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