1,2-Dichloroethane → HCID 86758314, compound

HRID 2228003Notes

Reaction equation

HRID 2228003 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:19][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:9]\[C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:39][O:40][C:41](=[O:49])[C@:42]([CH3:48])([CH2:44][CH2:45][S:46][CH3:47])[NH2:43].CN1CCOCC1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:19][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:9]\[C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH:43][C@@:42]([CH3:48])([CH2:44][CH2:45][S:46][CH3:47])[C:41]([O:40][CH3:39])=[O:49])=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 22944438HCID 22944438, compoundHCID 59117356HCID 59117356, compound

Product 1

HCID 86758314HCID 86758314, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (0.50 g, 1.55 mmol; prepared as the product of step D in Example 1), EDC (0.30 g, 1.55 mmol) and HOBt (0.21 g, 1.55 mmol) in dichloromethane (20 ml) was added α-methyl methionine methyl ester (0.33 g, 1.55 mmol) and 4-methylmorpholine (0.17 ml, 1.55 mmol). The solution was stirred at room temperature for 17 hrs, washed with brine (3×40 ml) dried over (MgSO4) and the solvent evaporated to leave a yellow gum. This was purified by chromatography (Biotage flash 40, 40 g SiO2 cartridge) eluting a gradient of 0-1% 0.88 aqueous ammonia/EtOAc to give the desired end product as a yellow gum 0.38 g (50%).

Workup

  1. washwashed with brine (3×40 ml)
  2. dry with materialdried over (MgSO4)
  3. customthe solvent evaporated
  4. customto leave a yellow gum
  5. customThis was purified by chromatography (Biotage flash 40, 40 g SiO2 cartridge)
  6. washeluting a gradient of 0-1% 0.88 aqueous ammonia/EtOAc

Sources & evidence

ORD record
ord-446d7d6cc65e4a52b60fbd49b27fe8d5
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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