Methanol → tert-butyl (2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-ylcarbamate

HRID 1025292Notes

Reaction equation

HRID 1025292 reaction equation
C([O:4][C@@H:5]([C@@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH3:14])[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)=[O:7])(=O)C.[OH-].[Na+].CO>O>[CH:9]1([NH:8][C:6](=[O:7])[C@@H:5]([OH:4])[C@@H:12]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:13][CH3:14])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86762403(2S,3S)-3-(tert-butoxycarbonylamino)-1-(cyclopropylamino)-1-oxopentan-2-yl acetate

Product 1

HCID 86762402tert-butyl (2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Under an atmosphere of argon, (2S,3S)-3-(tert-butoxycarbonylamino)-1-(cyclopropylamino)-1-oxopentan-2-yl acetate (1.09 g, 3.47 mmol, Eq: 1.00) and NaOH 1N in H2O (5.2 ml, 5.2 mmol, Eq: 1.5) were combined with methanol (10 ml) to give a colorless solution. The reaction was stirred for 2 h at RT. The reaction mixture was poured into 25 mL H2O and extracted with ethyl acetate (2×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a light brown solid (540 mg, 57.2%, MS (m/e)=273.4 [M+H+]).

Workup

  1. customto give a colorless solution
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1570a9c69d1415a852e945ab8da36ba
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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