1,2-Dichloroethane → HCID 57224478, 화합물

HRID 1251884노트

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HRID 1251884 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 57224478HCID 57224478, 화합물수율 79.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3f584ab5632b48fe98fac89d315ba2cb
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342765B1

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