Dicyclohexylcarbodiimide → benzyl [(R)-2-(1-allyl-1H-imidazol-4-yl)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

HRID 1023005Notes

Reaction equation

HRID 1023005 reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7]([CH2:9][C@@H:10]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C:11]([OH:13])=O)[N:6]=[CH:5]1)[CH:2]=[CH2:3].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:50]([O:53][CH2:54][C@@H:55]([NH2:59])[CH:56]([CH3:58])[CH3:57])[CH:51]=[CH2:52]>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@@H:10]([C:11](=[O:13])[NH:59][C@H:55]([CH2:54][O:53][CH2:50][CH:51]=[CH2:52])[CH:56]([CH3:58])[CH3:57])[CH2:9][C:7]1[N:6]=[CH:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 58360494(S)-1-Allyloxymethyl-2-methylpropylamineHCID 67029144(R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

Product 1

HCID 86655969benzyl [(R)-2-(1-allyl-1H-imidazol-4-yl)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the material from step A in 180 ml of DMF was mixed with 4.18 g (27.32 mmol) of N-hydroxybenzotriazole and 5.64 g (27.32 mmol) of N,N′-dicyclohexylcarbodiimide and stirred at RT for 2 h. Addition of 3.56 g (24.84 mmol) of (S)-1-allyloxymethyl-2-methylpropylamine (1-1B) was followed by stirring at RT for a further 24 h and then concentration, and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC. After washing with saturated NaHCO3 solution, 5.02 g of the title compound are obtained.

Workup

  1. stirringby stirring at RT for a further 24 h
  2. concentrationconcentration
  3. customthe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. washAfter washing with saturated NaHCO3 solution, 5.02 g of the title compound
  9. customare obtained

Sources & evidence

ORD record
ord-caebd65a19ac43ca94587d546f8cce0c
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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