Triethylamine → HCID 15660873, compound
Reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:16]([N:23]([CH3:31])[C:24]([CH2:26][CH2:27][C:28]([OH:30])=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[CH2:37][OH:38]>C1COCC1.O>[CH2:16]([N:23]([CH3:31])[C:24]([CH2:26][CH2:27][C:28]([N:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[CH2:37][OH:38])=[O:30])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
Triethylamine (4.0 ml) and isobutyl chloroformate (1.86 ml) were added dropwise to a solution of 3-(N-benzyl-N-methylcarbamoyl) propionic acid (2.5 g) in THF (30 ml) cooled to -20° C. The mixture was stirred for 30 mins at the same temperature. Triethylamine (4 ml) was added to a solution of (S)-2-pyrrolidinemethanol (1.45 g) in THF (30 ml). To the solution cooled to -25° C., the above solution was added dropwise. The mixture was stirred for 1 hr at the same temperature. After reaction, water was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (CH2Cl2 --CH3OH) to give the title compound (2.59 g) having the following physical data:
Workup
- temperatureTo the solution cooled to -25° C.
- additionthe above solution was added dropwise
- stirringThe mixture was stirred for 1 hr at the same temperature
- additionwas added to the reaction solution
- extractionThe mixture was extracted with EtOAc
- washThe extract was washed
- customdried
- customevaporated
- customThe residue was purified by column chromatography on silica gel (CH2Cl2 --CH3OH)
Sources & evidence
- ORD record
- ord-e409292c8a0f41f0a6dd4266421be39e
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05053414
Reaction notes
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