Sodium Hydroxide → 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoic acid

HRID 2071191Notes

Reaction equation

HRID 2071191 reaction equation
[OH:1][C@H:2]([CH2:24][NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:32]=1)[C@@H:3]([NH:11][C:12]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19]C)=[O:18])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>CO.C1COCC1>[OH:1][C@H:2]([CH2:24][NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:32]=1)[C@@H:3]([NH:11][C:12]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([OH:19])=[O:18])=[O:13])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68671696methyl 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoate

Product 1

HCID 686712363-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

methyl 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoate (0.060 g, 0.126 mmol, 1 eq) was dissolved in 2 ml of 1:1 MeOH/THF. 1N NaOH (0.158 ml, 0.158 mmol, 1.25 eq) was added and the reaction was stirred over the weekend. The solvent was removed in vacuo. 1N HCl was added to pH {tilde over ( )} 3-4. The mixture was diluted with 10% MeOH in CHCl3 and dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo yielding 0.055 g (0.119 mmol, 95% yield) of 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoic acid.

Workup

  1. customThe solvent was removed in vacuo
  2. addition1N HCl was added
  3. additionThe mixture was diluted with 10% MeOH in CHCl3
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0978de90961b4c53800a4b7a3b631965
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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