Triethylamine → HCID 495678, compound

HRID 1729211Notes

Reaction equation

HRID 1729211 reaction equation
C([N:3](CC)CC)C.[OH:8][CH:9]1[CH2:13][N:12]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)[CH:11]([C:25]([OH:27])=O)[CH2:10]1.ClC(OCC)=O>C(#N)C>[OH:8][CH:9]1[CH2:13][N:12]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)[CH:11]([C:25]([NH2:3])=[O:27])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16771157HCID 16771157, compound

Product 1

HCID 495678HCID 495678, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.1 equivalents of triethylamine are added to 4.5 g (0.016 mol) of the 4-hydroxy-1-[3,4-methylenedioxybenzoyl]pyrrolidine-2-carboxylic acid obtained in Example 5 suspended in 130 ml of acetonitrile at 0° C. The reaction mixture is stirred for 20 minutes and then 1.1 equivalents of ethyl chloroformate are added while maintaining the temperature between 0° and 5° C. After stirring for 20 minutes, ammonia is bubbled through the reaction mixture. The precipitate formed is separated. The filtrate is removed under vacuum, the precipitate obtained is recrystallized in acetonitrile.

Workup

  1. temperaturewhile maintaining the temperature between 0° and 5° C
  2. stirringAfter stirring for 20 minutes
  3. customammonia is bubbled through the reaction mixture
  4. customThe precipitate formed
  5. customis separated
  6. customThe filtrate is removed under vacuum
  7. customthe precipitate obtained
  8. customis recrystallized in acetonitrile

Sources & evidence

ORD record
ord-499c490d0dc24610a20b2e2c7eb98c42
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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