Anisole → trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline

HRID 1088252Notes

Reaction equation

HRID 1088252 reaction equation
COC1C=CC(C[O:8][C:9](=[O:37])[C@@H:10]2[CH2:14][C@@H:13]([O:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][N:11]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[N+:34]([C:31]1[CH:32]=[CH:33][C:28]([CH2:27][O:26][C:24]([N:11]2[CH2:12][C@H:13]([O:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][C@H:10]2[C:9]([OH:37])=[O:8])=[O:25])=[CH:29][CH:30]=1)([O-:36])=[O:35]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 15671448trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline p-methoxybenzyl ester

Product 1

HCID 14830184trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trans-1-(p-Nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline p-methoxybenzyl ester (61.3 g) and anisole (12.8 ml) were stirred together with 70 ml of trifluoroacetic acid at room temperature for 30 minutes. The reaction mixture was distilled to remove tri-fluoroacetic acid, and the residue was diluted with ethyl acetate and a saturated sodium bicarbonate solution. The precipitated crystals were separated by filtration and dissolved in methanol. The solution was acidified with 6N hydrochloric acid to pH 1.0, diluted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to give trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline.

Workup

  1. distillationThe reaction mixture was distilled
  2. customto remove tri-fluoroacetic acid
  3. additionthe residue was diluted with ethyl acetate
  4. customThe precipitated crystals were separated by filtration
  5. dissolutiondissolved in methanol
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-3a500549c8c64326a44bb8a936fb9003
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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