Triethylamine → HCID 15927688, compound

HRID 330623Notes

Reaction equation

HRID 330623 reaction equation
Br[CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:26]([O:30][C:31](=[O:42])[C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37](=[O:41])[C@H:38]([CH3:40])[NH2:39])([CH3:29])([CH3:28])[CH3:27].C(N(CC)CC)C>C(#N)C>[C:26]([O:30][C:31](=[O:42])[C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37](=[O:41])[C@H:38]([CH3:40])[NH:39][C@@H:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])([CH3:28])([CH3:27])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12939800tert-Butyl L-alanyl-L-prolinateHCID 13622534Ethyl 2-bromo-9-phthalimidononanoate

Product 1

HCID 15927688HCID 15927688, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 2-bromo-9-phthalimidononanoate [prepared according to Chem. Pharm. Bull. 34, 2078 (1986)] (3 g), L-alanyl-L-proline tertiary butylester (1 g) and triethylamine (0.8 ml) in acetonitrile (200 ml) is subjected to 60 hours' reflux. Acetonitrile is distilled off under reduced pressure, and the residue is dissolved in ethyl acetate. The solution is dehydrated with anhydrous sodium sulfate, and thereafter is concentrated to obtain an oily residue. When this substance is applied to a silica gel chromatography (ethyl acetate:n-hexane=3:1) for separative purification, 310 mg of N-[1(R)-ethoxycarbonyl-8-phthalimidooctyl]-L-alanyl-L-proline tertiary butylester is obtained as a colorless oil from the first effluence.

Workup

  1. temperature' reflux
  2. distillationAcetonitrile is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. concentrationis concentrated
  5. customto obtain an oily residue
  6. customWhen this substance is applied to a silica gel chromatography (ethyl acetate:n-hexane=3:1) for separative purification

Sources & evidence

ORD record
ord-634fc89166d84c45b81d6c9f9789ba58
Source dataset
uspto-grants-1990_01
Patent number
US04897483

Reaction notes

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