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

HRID 1587984Notes

Reaction equation

HRID 1587984 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aecfa8383748481794479d01586f3c34
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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