Sodium Hydroxide → (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate

HRID 2407842Notes

Reaction equation

HRID 2407842 reaction equation
[OH-:1].[Na+].[N+]([C:6]1C=CC=C[C:7]=1[C:8]([O-:10])=O)([O-])=O.[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30]([NH:32][C@@H:33]([CH2:41][SH:42])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:31])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1>CC(O)(C)C>[CH:24]1[C:25]2[CH:26]([CH2:28][O:29][C:30]([NH:32][C@@H:33]([CH2:41][S:42][CH2:6][C@H:7]([OH:1])[CH2:8][OH:10])[C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])=[O:31])[C:27]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 51598922-NitrobenzoateHCID 11440950(R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-mercaptopropanoate

Product 1

HCID 10412572(R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of (25)-(+)-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 vaccuo 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

  1. concentrationThe reaction mixture was concentrated en vaccuo
  2. customto remove tBuOH
  3. dissolutiondissolved in EtOAc
  4. washThe EtOAc solution was washed three times with water
  5. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-874177ebfd2e46d6b396903f0ff123a8
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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