HCID 23356894, compound → HCID 53970794, compound

HRID 233743Notes

Reaction equation

HRID 233743 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[N-:14]=[C:15]=[O:16].[CH3:17][O:18][C:19](=[O:26])[C@H:20]([C@H:22]([CH2:24][CH3:25])[CH3:23])N>C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH2:11][CH2:12][CH3:13])[C:15]([NH:14][C@H:20]([C:19]([O:18][CH3:17])=[O:26])[CH:22]([CH3:23])[CH2:24][CH3:25])=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23356894HCID 23356894, compoundHCID 86741872HCID 86741872, compound

Product 1

HCID 53970794HCID 53970794, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 0.73 g (3 mmol) of the compound from Example VI in 5 ml of ethyl acetate is added at 0° C. to a solution of 0.93 g (2.16 mmol) of (S)-isoleucine methyl ester isocyanate (prepared by reacting (S)-isoleucine methyl ester hydrochloride with trichloromethyl chloroformate in toluene at 120° C.) in 10 ml of ethyl acetate, and the mixture is stirred at this temperature for 30 min. Subsequently, the reaction mixture is washed successively with dilute hydrochloric acid, water and saturated solutions of sodium hydrogen carbonate and sodium chloride, and the organic phase is then concentrated and the residue purified on silica gel using petroleum ether/ethyl acetate (2:1).

Workup

  1. washSubsequently, the reaction mixture is washed successively with dilute hydrochloric acid, water and saturated solutions of sodium hydrogen carbonate and sodium chloride
  2. concentrationthe organic phase is then concentrated
  3. customthe residue purified on silica gel

Sources & evidence

ORD record
ord-e2352799e2df40d888d0ceb0a52e6f5c
Source dataset
uspto-grants-1997_01
Patent number
US05594010

Reaction notes

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