Triethylamine → HCID 19011717, compound

HRID 1729210Notes

Reaction equation

HRID 1729210 reaction equation
C([N:3](CC)CC)C.[OH:8][C@@H:9]1[CH2:13][N:12]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[C@@H:11]([C:26]([OH:28])=O)[CH2:10]1.ClC(OCC)=O>CC(C)=O>[OH:8][CH:9]1[CH2:13][N:12]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH:11]([C:26]([NH2:3])=[O:28])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30073917HCID 30073917, compound

Product 1

HCID 19011717HCID 19011717, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.1 equivalents of triethylamine are added to 3 g (0.01 mole) of the trans-4-hydroxy- 1-(3,4-dimethoxybenzoyl)pyrrolidine-2-carboxylic acid obtained in Example 4 in suspension of 200 ml of acetone 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° C. and 5° C. After stirring for 20 minutes, the mixture is filtered and ammonia is bubbled through the solution. The precipitate formed is separated, the acetone is removed under vacuum and the product obtained is recrystallized in water.

Workup

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

Sources & evidence

ORD record
ord-3034c89de48d48b9a47187e232c7a750
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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