Methyl iodide → 4-Methoxybenzyloxycarbonyl-(S)-isoserine methyl ester

HRID 274233Notes

Reaction equation

HRID 274233 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][O:14][C:15]([NH:17][CH2:18][C@@H:19]([C:21]([OH:23])=[O:22])[OH:20])=[O:16])=[CH:11][CH:10]=1.CI.CCOC(C)=O.CCCCCC>CO>[CH3:1][O:22][C:21](=[O:23])[C@@H:19]([OH:20])[CH2:18][NH:17][C:15]([O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:25][CH:24]=1)=[O:16]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 127738164-methoxybenzyloxycarbonyl-(S)-isoserineHCID 21226206Ethyl acetate hexane

Product 1

HCID 152840544-Methoxybenzyloxycarbonyl-(S)-isoserine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir cesium carbonate (6.2 g) and N-(4-methoxybenzyloxycarbonyl-(S)-isoserine (10 g) in dimethyl formamide(DMF) (50 ml) for 1 hr. then add methyl iodide (5.4 g). Stir the resulting mixture for 18 h and concentrate in vacuo. Partition the residue between EtOAc/water and then brine. Concentrate the dried (MgSO4) EtOAc solution in vacuo to give an amber oil. Chromatograph this oil on a column of flash silica gel (1100 ml) using EtOAc:hexane (9:1) as eluant to give an amber oil, [α]D26 =+16.9° (MeOH).

Workup

  1. concentrationconcentrate in vacuo
  2. customPartition the residue between EtOAc/water
  3. concentrationConcentrate the
  4. dry with materialdried (MgSO4) EtOAc solution in vacuo
  5. customto give an amber oil

Sources & evidence

ORD record
ord-e7a04939db35441888ce65ccbca04c21
Source dataset
uspto-grants-1995_02
Patent number
US05389610

Reaction notes

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