Methyl formate → HCID 45116049, compound

HRID 1078731Notes

Reaction equation

HRID 1078731 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.[CH:19](OC)=[O:20]>>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[CH:19]=[O:20]

Participants

4

Reactant 3

HCID 7865Methyl formateHCID 8471TriethylamineHCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

Product 1

HCID 45116049HCID 45116049, compoundYield 77.4%

Procedure

To a suspension of (2S,4R)-4-hydroxyproline methyl ester hydrochloride (9.08 g, 50.0 mmol) in methyl formate (90.0 ml) was added triethylamine (11.85 ml, 85.0 mmol). The mixture was refluxed for 5 h. The precipitate was filtered off, and the filtrate was concentrated in vacuo. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=4:1→3:2) to give (2S,4R)-N-formyl-4-hydroxyproline methyl ester (6.70 g, yield: 77.4%).

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9125f74f0d64e1f87ad3bacb026700e
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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