Pentafluorophenol → (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

HRID 651777Notes

Reaction equation

HRID 651777 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19](O)=[O:20])[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].FC1C(O)=C(F)C(F)=C(F)C=1F.Cl.C(N=C=NCCCN(C)C)C.Cl.[NH2:51][NH2:52]>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([NH:51][NH2:52])=[O:20])[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]

Participants

8

Reactant 4

HCID 13041PentafluorophenolHCID 115031Hydrazinium chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11418712(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid

Product 1

HCID 69709501(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 20 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in 200 ml of dimethylformamide was cooled to 0° C. under nitrogen and treated with 11.8 g of pentafluorophenol and 12.3 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred for 2.5 hours at 0° C. and then treated with 19.8 g of hydrazine hydrochloride and 33 ml of triethylamine. The mixture was left to warm to room temperature and was then stirred overnight. Evaporation gave a residue which was dissolved in ethyl acetate and washed with 2M aqueous hydrogen chloride, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. Evaporation gave a solid which was washed with ether/hexane (1:1) and dried to give 12.1 g of of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. waitThe mixture was left
  2. temperatureto warm to room temperature
  3. stirringwas then stirred overnight
  4. customEvaporation
  5. customgave a residue which
  6. washwashed with 2M aqueous hydrogen chloride, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  7. customEvaporation
  8. customgave a solid which
  9. washwas washed with ether/hexane (1:1)
  10. customdried

Sources & evidence

ORD record
ord-30cc4a093ad646fd95ab9889fdef551b
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

Loading…