Benzyl chloroformate → N-Methyl-N-[(phenylmethoxy)carbonyl]-L-glutamic acid
Reaction equation
[CH3:1][NH:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[CH2:21]([O:20][C:18]([N:2]([CH3:1])[C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-Methyl-L-glutamic acid (3.2 g) was added to water (50 ml) and the pH of the solution adjusted to 9 with solid sodium bicarbonate. The solution was cooled to 0° C. and stirred vigorously, while benzyl chloroformate (9 ml) was added dropwise over 20 min. The mixture was stirred for a further 2 h at 0° C. and an additional 2 h at room temperature, then extracted with diethyl ether (2×100 ml). The aqueous solution was then acidified to pH 3 with 5N HCl and the product isolated by extraction with ethyl acetate (2×100 ml). The pooled organic extracts were dried over anhydrous sodium sulphate and the solvent concentrated in vacuo to give a yellow oil, which crystallised on standing. Recrystallisation from water afforded N-(benzyloxycarbonyl)-N-methyl-L-glutamic acid (2.26 g), m.p. 97°-98° C.
Workup
- additionwas added dropwise over 20 min
- extractionextracted with diethyl ether (2×100 ml)
- customthe product isolated by extraction with ethyl acetate (2×100 ml)
- dry with materialThe pooled organic extracts were dried over anhydrous sodium sulphate
- concentrationthe solvent concentrated in vacuo
- customto give a yellow oil, which
- customcrystallised
- customRecrystallisation from water
Sources & evidence
- ORD record
- ord-86d2efa38466458a950734ed3bb10dd2
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561133
Reaction notes
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