Ethanol → 2-Amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([NH:26]C=O)[CH:6]=[C:7]([CH2:15][P:16]([O:22]C(C)C)([O:18]C(C)C)=[O:17])[CH2:8][CH2:9][CH2:10][O:11]C(=O)C)[CH3:2].C[Si](C)(C)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([NH2:26])[CH:6]=[C:7]([CH2:15][P:16]([OH:18])([OH:22])=[O:17])[CH2:8][CH2:9][CH2:10][OH:11])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4.3 g (9.9 mmol) of 7-acetoxy-4-diisopropylphosphonomethyl-2-formylamino-hept-3-enoic acid ethyl ester are dissolved in 25 ml of dichloromethane, and 5.1 ml (39.5 mmol) of trimethylbromosilane are added dropwise at room temperature. The mixture is left to stand at room temperature for 24 hours, 25 ml of ethanol are added dropwise, the mixture is left to stand for a further 24 hours and is concentrated by evaporation, the residue is dissolved in 25 ml of ethanol, and a mixture of 25 ml of propylene oxide and 25 ml of ethanol is added dropwise. A suspension forms, which is stirred for one hour at room temperature and for one hour in an ice bath and is then filtered with suction. Drying yields 2-amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid ethyl ester having a melting point of 210° C. (decomp.).
Workup
- waitThe mixture is left
- waitthe mixture is left
- waitto stand for a further 24 hours
- concentrationis concentrated by evaporation
- dissolutionthe residue is dissolved in 25 ml of ethanol
- additiona mixture of 25 ml of propylene oxide and 25 ml of ethanol
- additionis added dropwise
- filtrationis then filtered with suction
- customDrying
Sources & evidence
- ORD record
- ord-5af041dfda7142a292fa2c13f674f79f
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294734
Reaction notes
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