Triethylamine → HCID 15671478, compound

HRID 1088271Notes

Reaction equation

HRID 1088271 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:11].C(N(CC)CC)C.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 10804797HCID 10804797, compound

Product 1

HCID 15671478HCID 15671478, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

trans-1-(p-Methoxybenzyloxycarbonyl)-4-hydroxy-L-proline methyl ester (5.18 g), 3.79 g of triethylamine and 3.77 g of t-butyldimethylsilyl chloride were dissolved in 52 ml of dry dimethylformamide. The resulting mixture was stirred at room temperature for 3 hours, diluted with water, extracted with ethyl acetate, washed successively with water, dilute hydrochloric acid and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography to obtain trans-1-(p-methoxybenzyloxycarbonyl)-4-t-butyldimethylsilyloxy-L-proline methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed successively with water, dilute hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d075a0803094e93a8e9ab848cf4c6f3
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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