Sodium Hydroxide → HCID 57893118, compound

HRID 1511455Notes

Reaction equation

HRID 1511455 reaction equation
C([O:4][CH:5]([C@@H:12]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH:14]1[CH2:17][CH2:16][CH2:15]1)[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)=[O:7])(=O)C.[OH-].[Na+]>CO>[CH:14]1([CH2:13][C@H:12]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:5]([OH:4])[C:6]([NH:8][CH:9]2[CH2:10][CH2:11]2)=[O:7])[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57893114(3S)-3-(tert-butoxycarbonylamino)-4-cyclobutyl-1-(cyclopropylamino)-1-oxobutan-2-yl acetate

Product 1

HCID 57893118HCID 57893118, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S)-3-(tert-butoxycarbonylamino)-4-cyclobutyl-1-(cyclopropylamino)-1-oxobutan-2-yl acetate (3.8 g, 10.7 mmol) in methanol (50 mL) was added sodium hydroxide aqueous solution (1N, 15 mL) at room temperature. After 2 hours, methanol was removed under reduced pressure, and the concentrate was extracted with ethyl acetate. The ethyl acetate was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from 100 mL of ethyl acetate and hexane(v/v=3/1) to give tert-butyl (2S)-1-cyclobutyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-ylcarbamate (2.9 g) as a white solid.

Workup

  1. custommethanol was removed under reduced pressure
  2. extractionthe concentrate was extracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was crystallized from 100 mL of ethyl acetate and hexane(v/v=3/1)

Sources & evidence

ORD record
ord-8c8c298723ee4e1db462305b31f299cd
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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