Triethylamine → HCID 86756887, compound

HRID 1979198Notes

Reaction equation

HRID 1979198 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].C(N(CC)CC)C.[NH:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[C:46](O)=[O:47].ClCCl.CO>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:46]([C:42]1[NH:41][CH:45]=[CH:44][CH:43]=1)=[O:47])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12473Pyrrole-2-Carboxylic AcidHCID 21226129Dichloromethane methanolHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756887HCID 86756887, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.459 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of dichloromethane was treated under nitrogen at 0° C. with 0.28 ml of triethylamine and a solution of the acid chloride prepared from 0.166 g of 2-pyrrolecarboxylic acid in 3 ml of dichloromethane. The mixture was stirred at 0° C. for 2 hours and evaporated. The residue was dissolved in ethyl acetate. The solution was washed with 5% aqueous sodium hydrogen carbonate solution, water, 5% citric acid solution and saturated sodium chloride solution, dried over anhydrous magnesium sulphate and was evaporated to give a solid. Chromatography of this solid on silica gel using dichloromethane/methanol (50:1) for the elution followed by evaporation and trituration with diethyl ether gave 0.225 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-[(2-pyrrolyl)carbonyl]valerohydrazide in the form of a white solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 5% aqueous sodium hydrogen carbonate solution, water, 5% citric acid solution and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customwas evaporated
  6. customto give a solid
  7. washfor the elution
  8. customfollowed by evaporation and trituration with diethyl ether

Sources & evidence

ORD record
ord-e4bb9d383ca34d328eee96ad646861fd
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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