HCID 131725395, compound → HCID 131725394, compound

HRID 1745011Notes

Reaction equation

HRID 1745011 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][N:9]1C(OC(C)(C)C)=O)=[O:7]>CCOCC>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][NH:9]1)=[O:7]

Participants

3

Reactant 1

HCID 131725395HCID 131725395, compound

Product 1

HCID 131725394HCID 131725394, compoundYield 1,393.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution was made containing the amide compounds from the previous step, e.g. tert-butyl (2S,4EZ)-2-{[(2-methoxyethyl)amino]carbonyl}-4-(methoxyimino)-1-pyrrolidine-carboxylate (1.5 g, 0.4 mmol), in anhydrous ether (35 ml). HCl gas was bubbled slowly through the reaction and the deprotection was followed by TLC. After approximately 20 minutes, the ether was evaporated. The product was concentrated in vacuo from DCM (2–3 times) to remove the HCl. The desired product, e.g. (2S,4EZ)-N-(2-methoxyethyl)-4-(methoxyimino)-2-pyrrolidinecarboxamide (1.2 g, quant.) was isolated as a yellow oil and used without further purification.

Workup

  1. customHCl gas was bubbled slowly through the reaction
  2. customthe ether was evaporated
  3. concentrationThe product was concentrated in vacuo from DCM (2–3 times)
  4. customto remove the HCl

Sources & evidence

ORD record
ord-a4812d809d8945be9f2b7783c60c05e3
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

Loading…