Triethylamine → HCID 70072902, compound

HRID 1977585Notes

Reaction equation

HRID 1977585 reaction equation
OC(CC(=N)O)C(=N)O.[CH2:10]([O:12][C:13]([NH:15][C@@H:16]([C:24]([OH:26])=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH3:11].[NH:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30].C(N(CC)CC)C>N1C=CC=CC=1>[CH2:10]([O:12][C:13]([NH:15][C@@H:16]([C:24]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30])=[O:26])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145742L-ProlineHCID 178473528HCID 178473528, compound

Product 1

HCID 70072902HCID 70072902, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.34 g (10 mmol) of ethoxycarbonyl-3-phenyl-D-alanine hydroxysuccinimidate (Synthesis 1, Step B) is dissolved in 15 ml of pyridine and 1.15 g (10 mmol) of L-proline and 1.4 ml (10 mmol) of triethylamine are added. The reaction mixture is stirred at room temperature for 10 hours, then evaporated at a pressure of 2.0-2.5 kPa. The residue is distributed between 30 ml 5% NaHCO3 solution and 10 ml of diethyl ether. The aqueous phase is washed with 3×5 ml of diethyl ether, the pooled organic washings are extracted with 5 ml 5% NaHCO3-solution. The bicarbonate phases are pooled, acidified with 1M KHSO4 solution to pH3 and extracted with 3×10 ml of ethyl acetate. The pooled organic extracts are dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The oily residue is crystallised with diethyl ether, the crystals are filtered, washed with diethyl ether and dried in a vacuum desiccator.

Workup

  1. customevaporated at a pressure of 2.0-2.5 kPa
  2. washThe aqueous phase is washed with 3×5 ml of diethyl ether
  3. extractionthe pooled organic washings are extracted with 5 ml 5% NaHCO3-solution
  4. extractionextracted with 3×10 ml of ethyl acetate
  5. dry with materialThe pooled organic extracts are dried over anhydrous sodium sulphate
  6. customevaporated at a pressure of 2.0-2.5 kPa
  7. customThe oily residue is crystallised with diethyl ether
  8. filtrationthe crystals are filtered
  9. washwashed with diethyl ether
  10. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-71634b4eaa884b6881dc360bab0b6392
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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