Dichloromethane → HCID 56648017, compound
Reaction equation
[C:1]1([C:7]2([C:10]([OH:12])=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.ON1C2C=CC=CC=2N=N1.[NH2:38][C@H:39]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:40][N:41]1[CH2:45][CH2:44][C@H:43](O)[CH2:42]1.C(Cl)[Cl:54]>>[ClH:54].[C:1]1([C:7]2([C:10]([NH:38][C@@H:39]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:40][N:41]3[CH2:42][CH2:43][CH2:44][CH2:45]3)=[O:12])[CH2:8][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
To a solution of 1-phenylcyclopropanecarboxylic acid (1 eq.), were added at about 20-35° C., DCC (1 eq) in DCM and 1-Hydroxybenzotriazole (1 eq.). The mixture was stirred for 10 min and to this mixture was added (S)-1-((R)-2-amino-2-phenylethyl)pyrrolidin-3-ol (1 eq) and the contents were allowed to stir at about 20-35° C. for 12 h. The reaction mixture was filtered, the filtrate was diluted with DCM and the organic layer was washed with sat.NaHCO3 solution, brine and dried over Na2SO4 and concentrated under reduced pressure to give the crude product. The crude was purified by flash chromatography using silica gel (230-400 mesh) to give the desired product as a pale yellow gum. The resultant product is treated with hydrochloric acid to form the corresponding hydrochloric acid salt by following standard salt forming procedures known in the art.
Workup
- stirringto stir at about 20-35° C. for 12 h
- filtrationThe reaction mixture was filtered
- additionthe filtrate was diluted with DCM
- washthe organic layer was washed
- dry with materialNaHCO3 solution, brine and dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customto give the crude product
- customThe crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-1e0ba6bf393248a29d27a0438758023c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303027B2
Reaction notes
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