Triethylamine → trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

HRID 2107492Notes

Reaction equation

HRID 2107492 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][O:15][C:14](=[O:16])[C@@H:13]2[CH2:17][C@@H:18]([OH:20])[CH2:19][N:12]2[C:10]([O:9][CH2:8][C:7]2[CH:21]=[CH:22][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 13504318trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

15.0 g of trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline and 13.5 ml of triethylamine were dissolved in 150 ml of dried dimethylformamide, and 12.66 ml of p-methoxybenzyl chloride was added dropwise to the solution under a nitrogen stream, followed by stirring at 70° C. for 10 hours. The reaction mixture was diluted with 500 ml of ethyl acetate, washed with water, dried over sodium sulfate and distilled off to remove the solvent. Recrystallization of the residue from diethyl ether gave trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. distillationdistilled off
  4. customto remove the solvent
  5. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-e01e5681e4cb4f9c90236c6cbda4fe9b
Source dataset
uspto-grants-1990_06
Patent number
US04933333

Reaction notes

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