Triethylamine → (2S, 4R)-4-hydroxy-N-(4-nitrobenzyloxycarbonyl)proline methyl ester

HRID 1195658Notes

Reaction equation

HRID 1195658 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.C(N(CC)CC)C.CC1C=C(C)N=C(S[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])N=1>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=1)=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideHCID 135043164,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidine

Product 1

HCID 18656014(2S, 4R)-4-hydroxy-N-(4-nitrobenzyloxycarbonyl)proline methyl esterYield 81.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a clear solution of L-hydroxyproline methyl ester hydrochloride (27.2 g, 0.15 mol) and triethylamine (50 ml, 0.36 mol) in chloroform (500 ml) was added 4,6-dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidine (40.7 g, 0.13 mol) and then the resulting solution was stirred at room temperature for 12 hours, sequentially washed with H2O (200 ml), 0.5N NaOH (400 ml) and brine (200 ml) and dried (MgSO4). Concentration followed by silicagel column chromatography (Wakogel® C-300, ethyl acetate) afforded (2S, 4R)-4-hydroxy-N-(4-nitrobenzyloxycarbonyl)proline methyl ester (34.5 g, 70.9% yield) as an oil.

Workup

  1. washsequentially washed with H2O (200 ml), 0.5N NaOH (400 ml) and brine (200 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationConcentration

Sources & evidence

ORD record
ord-659e3c238d034dea8a9a2a5f2ad9423d
Source dataset
uspto-grants-1992_05
Patent number
US05112818

Reaction notes

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