4-Methylmorpholine → N-[2(S)-Acetylthiomethyl-3-(2-methylphenyl)-propanoyl]-(S)-isoserine ethyl ester

HRID 1587984ノート

反応式

HRID 1587984 の反応式
[C:1]([S:4][CH2:5][C@@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:7]([OH:9])=O)(=[O:3])[CH3:2].Cl.[CH2:19]([O:21][C:22](=[O:27])[C@@H:23]([OH:26])[CH2:24][NH2:25])[CH3:20].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.C(Cl)CCl>[CH2:19]([O:21][C:22](=[O:27])[C@@H:23]([OH:26])[CH2:24][NH:25][C:7](=[O:9])[C@@H:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH3:20]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 228417862(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acidHCID 86746976(S)-isoserine ethyl ester hydrochloride

生成物 1

HCID 18652470N-[2(S)-Acetylthiomethyl-3-(2-methylphenyl)-propanoyl]-(S)-isoserine ethyl ester

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

実験手順

Combine 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (1.65 g) and (S)-isoserine ethyl ester hydrochloride (1.10 g), EDC (1.51 g), HOBT (0.99 g) and N-methylmorpholine (1.50 ml) in DMF (10 ml), and stir the resulting mixture for 20 hours. Concentrate the reaction mixture in vacuo and partition the residue between dichloromethane/water. Concentrate the dried (MgSO4) dichloromethane solution in vacuo. Chromatograph the resulting residue on a column of flash silica gel (300 ml) using ethyl acetate:hexane (1:3); ethyl acetate; ethyl acetate:methanol (9:1) as eluant to give the title compound, a colorless oil, [α]D26 =0° (MeOH).

後処理

  1. concentrationConcentrate the reaction mixture in vacuo
  2. custompartition the residue between dichloromethane/water
  3. concentrationConcentrate the
  4. dry with materialdried (MgSO4) dichloromethane solution in vacuo

出典と根拠

ORDレコード
ord-aecfa8383748481794479d01586f3c34
出典データセット
uspto-grants-1993_06
特許番号
US05219886

反応ノート

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