Triethylamine → HCID 19011692, compound

HRID 1729208Notes

Reaction equation

HRID 1729208 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:20])[C:8]2[CH:13]=[C:12]3[O:14][CH2:15][O:16][C:11]3=[CH:10][C:9]=2[N+:17]([O-:19])=[O:18])[C@@H:4]([C:21]([OH:23])=O)[CH2:3]1.C([N:26](CC)CC)C.ClC(OCC)=O>C(#N)C>[OH:1][CH:2]1[CH2:6][N:5]([C:7](=[O:20])[C:8]2[CH:13]=[C:12]3[O:14][CH2:15][O:16][C:11]3=[CH:10][C:9]=2[N+:17]([O-:19])=[O:18])[CH:4]([C:21]([NH2:26])=[O:23])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67822507HCID 67822507, compound

Product 1

HCID 19011692HCID 19011692, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

5 g (0.015 mole) of trans-4-hydroxy-1-(4,5-methylenedioxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid obtained in Example 1 are suspended in 130 ml of acetonitrile at room temperature and then 2.25 ml (0.015 mole) of triethylamine are added. After 30 minutes of stirring starting from the end of the addition, 1.5 ml (0.015 mol) of ethyl chloroformate are added into the suspension previously cooled at 5° C. The reaction mixture is again stirred for 30 minutes. Ammonia is bubbled through this solution, the temperature of which is maintained between 0° C. and 5° C. A precipitate appears. It is spun, washed with ether and recrystallized in acetonitrile.

Workup

  1. additionare added into the suspension
  2. stirringThe reaction mixture is again stirred for 30 minutes
  3. customAmmonia is bubbled through this solution
  4. temperaturethe temperature of which is maintained between 0° C. and 5° C
  5. washwashed with ether
  6. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-5dc0a21914864490a9603d21d3e43a7c
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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