Pyridine → (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate
Reaction equation
N1C=CC=CC=1.[OH-:7].[Na+].[N+]([C:12]1C=CC=C[C:13]=1[C:14]([O-:16])=O)([O-])=O.[CH:21]1[C:33]2[CH:32]([CH2:34][O:35][C:36]([NH:38][C@@H:39]([CH2:47][SH:48])[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:37])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1>CC(O)(C)C>[CH:30]1[C:31]2[CH:32]([CH2:34][O:35][C:36]([NH:38][C@@H:39]([CH2:47][S:48][CH2:12][C@H:13]([OH:7])[CH2:14][OH:16])[C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])=[O:37])[C:33]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2S)-(+)-glycidyl-4-nitrobenzoate (9, 1.1 eq) and 1M NaOH (1.1 eq) in tBuOH (0.1 M) was stirred at room temperature until complete hydrolysis of the nitrobenzoate (30 minutes). To the resulting mixture, a solution of (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate (8, 1 eq) in tBuOH (1 M) was introduced. The reaction was stirred at room temperature for 15 hours. The reaction mixture was concentrated en vacuo to remove tBuOH and dissolved in EtOAc. The EtOAc solution was washed three times with water, and once with brine. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-90% EtOAc/Hex to give the title product as colorless viscous oil.
Workup
- concentrationThe reaction mixture was concentrated en vacuo
- customto remove tBuOH
- dissolutiondissolved in EtOAc
- washThe EtOAc solution was washed three times with water
- customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)
Sources & evidence
- ORD record
- ord-a8f6b5b8d33c41479b288297c7f832ea
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315530B2
Reaction notes
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