1,2-Dichloroethane → HCID 59117364, compound

HRID 2228030Notes

Reaction equation

HRID 2228030 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][C:16](/[CH:19]=[C:20](\[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)/[CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[CH:15][C:11]=2[C:12](O)=[O:13])=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:49][O:50][C:51](=[O:58])[C@H:52]([CH2:54][CH2:55][S:56][CH3:57])[NH2:53].CN1CCOCC1>CN(C1C=CN=CC=1)C.ClCCl>[F:33][C:30]1[CH:31]=[CH:32][C:27](/[C:20](/[CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:19]\[C:16]2[CH:17]=[CH:18][C:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:11]([CH:15]=2)[C:12]([NH:53][C@@H:52]([CH2:54][CH2:55][S:56][CH3:57])[C:51]([O:50][CH3:49])=[O:58])=[O:13])=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 59117387HCID 59117387, compound

Product 1

HCID 59117364HCID 59117364, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-[(E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)prop-1-en-1-yl]benzoic acid (0.3 g; 0.67 mmol), EDC (0.154 g; 0.8 mmol), HOBT (0.108 g; 0.8 mmol), DMAP (0.090 g; 0.74 mmol), L-methionine methyl ester hydrochloride (0.2 g; 1 mmol) and N-Methylmorpholine (110 μl; 1 mmol) in dichloromethane (20 ml) was stirred at room temperature overnight. The organic phase was washed with aqueous sodium bicarbonate, dried and evaporated. The residue was purified by flash chromatography. eluting with a gradient of dichloromethane/ethanol (1-3%) to give methyl (2S)-2-{5-[(E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(2-(4-fluorophenyl)ethyl)benzamido}-4-methylsulfanylbutyrate as a white solid foam Yield=50%.

Workup

  1. washThe organic phase was washed with aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with a gradient of dichloromethane/ethanol (1-3%)

Sources & evidence

ORD record
ord-5f95cb88a881420d8944e47e1a296a8d
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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