Dicyclohexylcarbodiimide → HCID 86606570, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:34][O:35][CH2:36][CH2:37][C:38](O)=[O:39]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([C:6]#[N:7])[NH:8][C:38](=[O:39])[CH2:37][CH2:36][O:35][CH3:34])[CH3:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of aminocyanacetic acid ethyl ester (1.00 g, 7.80 mmol) in ethyl acetate (16.00 ml) was cooled to 0° C. and treated with dimethylaminopyridine (0.09 g, 0.78 mmol) and dicyclohexylcarbodiimide (1.93 g, 9.36 mmol). 3-Methoxy-propionic acid (0.81 g, 7.80 mmol) was added portionwise. After completed addition, the mixture was stirred at 0° C. for 1 h) then at room temperature for 3 h. The precipitated dicyclohexylurea was filtered off and the mother liquors washed with water, dried over sodium sulphate and evaporated. The residue was purified by trituration in diisopropylether to yield cyano-(3-methoxy-propionylamino)-acetic acid ethyl ester (1.27 g, 76%), MS (ISP): m/e=215.3 (M+H+).
Workup
- additionaddition
- filtrationThe precipitated dicyclohexylurea was filtered off
- washthe mother liquors washed with water
- dry with materialdried over sodium sulphate
- customevaporated
- customThe residue was purified by trituration in diisopropylether
Sources & evidence
- ORD record
- ord-1e881876bffc4eee9e5e31b83cc9d282
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678815B2
Reaction notes
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