4-Methylmorpholine → (E)-2'-benzyl-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

HRID 1979220Notes

Reaction equation

HRID 1979220 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([OH:21])=O)[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.Cl.Cl.[CH2:35]([NH:42][NH2:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH2:35]([NH:42][NH:43][C:19](=[O:21])[C@@H:18]([C@@H:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 146540Benzylhydrazine dihydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11418712(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid

Product 1

HCID 86756916(E)-2'-benzyl-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazideYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixure of 3.46 g of (E)-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid, 4.0 g of N-methyl morpholine, 2.95 g of benzylhydrazine dihydrochloride and 1.7 g of 1-hydroxybenzotriazole hydrate in 25 ml of dimethylformamide was cooled to 0° C. while stirring under nitrogen and 2.4 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide were added. The mixture was gradually allowed to come to room temperature and was then stirred overnight. The dimethylformamide was evaporated and the residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The ethyl acetate phase was washed in sequence with water, 5% citric acid solution, water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate the ethyl acetate was evaporated to give a yellow gum. Crystallization from hexane gave 1.87 g of (E)-2′-benzyl-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide as a white solid.

Workup

  1. customto come to room temperature
  2. stirringwas then stirred overnight
  3. customThe dimethylformamide was evaporated
  4. customthe residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution
  5. washThe ethyl acetate phase was washed in sequence with water, 5% citric acid solution, water and saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous magnesium sulphate the ethyl acetate
  7. customwas evaporated
  8. customto give a yellow gum
  9. customCrystallization from hexane

Sources & evidence

ORD record
ord-a114355babc648cc910f5c153acda4e2
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…