4-Methylmorpholine → {(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

HRID 1158505

Reaction equation

HRID 1158505 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[Br:47][C:48]1[CH:56]=[CH:55][C:51]([CH2:52][NH:53][NH2:54])=[CH:50][CH:49]=1>CCOC(C)=O>[CH2:4]([O:3][C:1](=[O:2])[NH:11][C@H:12]([C:16]([NH:54][NH:53][CH2:52][C:51]1[CH:55]=[CH:56][C:48]([Br:47])=[CH:49][CH:50]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 167731114-Bromobenzylhydrazine

Product 1

HCID 11532141{(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Cbz-(L)-Valine (1.04 g, 4.14 mmol) was dissolved in EtOAc (50 mL) and EDAC (0.870 g, 4.54 mmol), HOBT (0.610 g, 4.51 mmol), and NMM (0.500 mL, 4.55 mmol) were added. The reaction mixture was stirred at room temperature for 30 min and then 4-bromo-benzylhydrazine (1.00 g, 4.97 mmol) in EtOAc (5 mL) was added and the stirring was continued for 2 h. After evaporation of the solvent, CHCl3 was added and the solution was washed with saturated NaHCO3 (aq.) and brine followed by drying (Na2SO4), filtration and evaporation of the organic solvent. The crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5) yielding the title compound (1.42 g, 79%) as a white solid.

Workup

  1. waitthe stirring was continued for 2 h
  2. customAfter evaporation of the solvent, CHCl3
  3. additionwas added
  4. washthe solution was washed with saturated NaHCO3 (aq.) and brine
  5. customby drying
  6. filtration(Na2SO4), filtration and evaporation of the organic solvent
  7. customThe crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5)

Sources & evidence

ORD record
ord-0df577dc0a4546529ac95ddd46b4284f
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Linked notes

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