Benzoyl chloride → trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline p-methoxybenzyl ester

HRID 1088251Notes

Reaction equation

HRID 1088251 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@@H:13]([O:15][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 13504318trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Trans-1-(p-Nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester (49 g) was dissolved in 300 ml of dry tetrahydrofuran, and 33 ml of triethylamine, 9.59 g of 4-dimethylaminopyridine and 33.2 g of benzoyl chloride were added thereto, followed by stirring under reflux for 5 hours. The reaction mixture was cooled down to room temperature and distilled to remove the solvent. The residue was diluted with ethyl acetate, washed successively with water, dilute hydrochloric acid, water, a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. Recrystallization of the residue from diethyl ether gave trans-1-(p-nitrobenzyloxycarbonyl)-4-benzoyloxy-L-proline p-methoxybenzyl ester.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed successively with water, dilute hydrochloric acid, water
  6. dry with materiala saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-8ef5f1f51d5746f2a52764a982da7b55
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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