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

HRID 2407948Notes

Reaction equation

HRID 2407948 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 67400883(R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of (25)-(+)-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 the nitrobenzoate was observed (30 minutes). To the resulting mixture, a solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-mercaptopropanoate (12, 1 eq) in tBuOH (1 M) was introduced and the reaction stirred at room temperature for 15 hours. The reaction mixture was concentrated en vaccuo to remove tBuOH then dissolved in EtOAc. The EtOAc solution was washed three times with water, once with brine, then dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-90% EtOAc/Hex to give the title product as a colorless viscous oil.

Workup

  1. custom(30 minutes)
  2. concentrationThe reaction mixture was concentrated en vaccuo
  3. customto remove tBuOH
  4. dissolutionthen dissolved in EtOAc
  5. washThe EtOAc solution was washed three times with water
  6. dry with materialonce with brine, then dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-4d62bb6e612445af843f7746baf89690
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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