Potassium Carbonate → 2-(Dipropylamino)-2-oxoethyl 3-(((benzyloxy)carbonyl)amino)propanoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:16])C(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].Cl[CH2:24][C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26]>CN(C=O)C.O>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([CH2:24][O:18][C:17](=[O:20])[CH2:16][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:26])[CH2:29][CH3:30]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a solution of benzyloxycarbonylamino-propionic acid (22.3 g, 99.9 mmol) in DMF (150 ml) was added potassium carbonate (19.3 g, 139.9 mmol). 2-Chloro-N,N-dipropyl-acetamide (17.7 g, 99.9 mmol) was added over 30 min, and the reaction mixture was heated to 60° C. and stirred for 2.5 h. The reaction mixture was allowed to cool to RT and diluted with water (500 ml) and extracted with isopropyl acetate (total 500 ml). The combined organic phases were washed with water (3×200 ml) to afford a solution of 3-benzyloxycarbonylamino-propionic acid dipropylcarbamoylmethyl ester in isopropyl acetate which was not isolated further. LC-MS; 365.2 [M+H]+ Method (i)
Workup
- temperatureto cool to RT
- extractionextracted with isopropyl acetate (total 500 ml)
- washThe combined organic phases were washed with water (3×200 ml)
Sources & evidence
- ORD record
- ord-b8bf382323914e69bb2b9bd4c237fa1b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809340B2
Reaction notes
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