4-Methylmorpholine → N-[2(R,S)-Acetylthiomethyl-3-phenylpropanoyl]-(S)-isoserine benzyl ester

HRID 1587983Notes

Reaction equation

HRID 1587983 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].Cl.[CH2:18]([O:25][C:26](=[O:31])[C@@H:27]([OH:30])[CH2:28][NH2:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH2:18]([O:25][C:26](=[O:31])[C@@H:27]([OH:30])[CH2:28][NH:29][C:7](=[O:9])[CH:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 131717979benzyl (2S)-3-amino-2-hydroxypropanoate hydrochloride

Product 1

HCID 131717981N-[2(R,S)-Acetylthiomethyl-3-phenylpropanoyl]-(S)-isoserine benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 2(R,S)-acetylthiomethyl-3-phenylpropionic acid (0.59 g) to (S)-isoserine benzyl ester, hydrochloride (0.578 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.53 g), 1-hydroxybenzotriazole (HOBT) (0.37 g) and N-methylmorpholine (0.80 ml) in dimethylformamide (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 silica gel (1 L) using chloroform:methanol 19.5:1 as eluant to give the title compound, a colorless oil, [α]D26 =+12.3° (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-94ea739745a14c60a62f47c9d46ab26b
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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