1,2-Dichloroethane → HCID 57224478, compound

HRID 1251884Notes

Reaction equation

HRID 1251884 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:3]=1.CN1CCOCC1.Cl.[CH3:26][O:27][C:28](=[O:35])[C@H:29]([CH2:31][CH2:32][S:33][CH3:34])[NH2:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C@@H:29]([CH2:31][CH2:32][S:33][CH3:34])[C:28]([O:27][CH3:26])=[O:35])=[O:8])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 23499550HCID 23499550, compound

Product 1

HCID 57224478HCID 57224478, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-2-(4-fluorophenyl)benzoic acid (4.5 g; 0.019 mol) in DMF (90 ml) cooled to 0° C. under an argon atmosphere was added in sequence NMM (6.4 ml; 0.058 mol), L-methionine methyl ester hydrochloride (4.0 g; 0.020 mol), EDC (4.47 g; 0.023 mol) and HOBT (2.7 g; 0.020 mol) and the reaction warmed to ambient temperature and stirred for 3 hours. The DMF was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and brine, filtered through PSI filter paper and concentrated in vacuo to give a yellow oil. Purification by flash column chromatography eluting with ethyl acetate/iso-hexane (1:1) gave methyl (2S)-2-[4-hydroxy-2-(4-fluorophenyl)benzoylamino]-4-methylsulfanylbutyrate as a white foam (5.7 g).

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine
  4. filtrationfiltered through PSI
  5. filtrationfilter paper
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customPurification by flash column chromatography
  9. washeluting with ethyl acetate/iso-hexane (1:1)

Sources & evidence

ORD record
ord-3f584ab5632b48fe98fac89d315ba2cb
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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