5-Chloro-N-((S)-2,3-dihydroxypropyl)thiophene-2-carboxamide → 5-Chloro-N-((2R)-2-hydroxy-3-((4-(3-oxo-4-morpholinyl)phenyl)amino)propyl)-2-thiophenecarboxamide
Reaction equation
[OH:1][C@H:2]([CH2:13]O)[CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:6].BrC[C@@H](O)CNC(C1SC(Cl)=CC=1)=O.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C:37]2=[O:42])=[CH:32][CH:31]=1>>[OH:1][C@H:2]([CH2:13][NH:29][C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C:37]2=[O:42])=[CH:34][CH:35]=1)[CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:6]Participants
4
Reactant 3
Product 1
Procedure
In this case, 5-chlorothiophene-2-carbonyl chloride (IV) is reacted with (28)-3-aminopropane-1,2-diol hydrochloride (VII) to give 5-chlorothiophene-2-carboxylic acid ((S)-2,3-dihydroxypropyl)-amide (IX). Subsequently, (IX) is converted into 5-chlorothiophene-2-carboxylic acid ((S)-3-bromo-2-hydroxypropyl)amide (X), which is then reacted with 4-(4-aminophenyl)-3-morpholinone (III) to give 5-chlorothiophene-2-carboxylic acid {(R)-2-hydroxy-3-[4-(3-oxomorpholin-4-yl)phenylamino]-propyl}amide (XI). Finally, (XI) is reacted with phosgene or a phosgene equivalent to give 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide (I).
Sources & evidence
- ORD record
- ord-159151f55feb40e6ac45b3ce4c151abb
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351823B2
Reaction notes
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