Lithium Hydroxide → HCID 86702355, compound

HRID 1477156Notes

Reaction equation

HRID 1477156 reaction equation
C([O:8][C:9](=[O:28])[C@@H:10]([NH:14][C:15](=[O:27])[C@@H:16]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH3:17])[CH:11]([CH3:13])[CH3:12])C1C=CC=CC=1.[OH-].[Li+]>C1COCC1.CO.O>[C:23]([O:22][C:20]([N:18]([CH3:19])[C@@H:16]([CH3:17])[C:15]([NH:14][C@@H:10]([CH:11]([CH3:12])[CH3:13])[C:9]([OH:28])=[O:8])=[O:27])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117871378(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid benzyl ester

Product 1

HCID 86702355HCID 86702355, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid benzyl ester (7 g, 18 mmol) and 1 M aqueous lithium hydroxide (40 mL, 40 mmol) was added to THF/MeOH/H2O (3:1:1; 200 mL) to give a yellow solution. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in water and then acidified to pH 2 using first 6 M and then 1 M aqueous HCl. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give crude (S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid (5.7 g) which was used directly in the next step without further purification, m/z=303 (M+H).

Workup

  1. customto give a yellow solution
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f12e7ce2984b49c1b806593c30d0e19f
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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