Sodium Hydroxide → (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((S)-2,3-dihydroxypropylthio)propanoate

HRID 2407875Notes

Reaction equation

HRID 2407875 reaction equation
[OH-:1].[Na+].[N+]([C:6]1C=CC=C[C:7]=1[C:8]([O-:10])=O)([O-])=O.[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][SH:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(O)(C)C>[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][S:35][CH2:6][C@@H:7]([OH:1])[CH2:8][OH:10])[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 51598922-NitrobenzoateHCID 86678278tert-butyl (2R)-2-{[(benzyloxy)carbonyl]amino}-3-sulfanylpropanoate

Product 1

HCID 67402221(R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((S)-2,3-dihydroxypropylthio)propanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of (2R)-(−)-glycidyl-4-nitrobenzoate (1.1 eq) and 1M NaOH (1.1 eq) in tBuOH (0.1 M) was stirred at room temperature until complete hydrolysis of nitrobenzoate (30 min) was achieved. To the resulting mixture, a solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-mercaptopropanoate (1 eq) in tBuOH (1 M) was introduced. The reaction was stirred at room temperature for 15 hours, and concentrated en vaccuo to remove tBuOH; then the resulting residue was dissolved in EtOAc. The EtOAc solution was washed three times with H2O then once with brine. The organic layer was dried over anhydrous Na2SO4 then concentrated en vaccuo. The resulting crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-90% EtOAc/Hex to give the title compound as a colorless viscous oil.

Workup

  1. concentrationconcentrated en vaccuo
  2. customto remove tBuOH
  3. dissolutionthen the resulting residue was dissolved in EtOAc
  4. washThe EtOAc solution was washed three times with H2O
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationthen concentrated en vaccuo
  7. customThe resulting crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-450cf970c8064be591db421ef4e3cc4c
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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