Triethylamine → HCID 69943705, compound

HRID 744880Notes

Reaction equation

HRID 744880 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][C@H:15]([OH:19])[C:16]([OH:18])=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.COC1C=CC(COC([N:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)=O)=CC=1.C(N(CC)CC)C>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][C@H:15]([OH:19])[C:16]([N:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)=[O:18])=[O:11])=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 22600025(4-Methoxyphenyl)methyl piperazine-1-carboxylateHCID 57293013HCID 57293013, compound

Product 1

HCID 69943705HCID 69943705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.9 g of (2S)-4-(p-nitrobenzyloxycarbonyl)amino-2-hydroxybutyric acid dissolved in tetrahydrofuran were added, with cooling on an ice bath, 0.36 g of N-hydroxysuccunimide and 0.65 g of dicyclohexylcarbodiimide, followed by overnight reaction with stirring. To the solution were added 0.75 g of 1-(p-methoxybenzyloxycarbonyl)piperazine and 0.31 g of triethylamine, followed by 2 hours of reaction. After removal of insoluble material from the reaction mixture by filtration and subsequent concentration of the filtrate, a residue was mixed with ethyl acetate, washed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order and then dried over sodium sulfate, followed by evaporation of the solvent under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography to yield 1.33 g of 1-(p-methoxybenzyloxycarbonyl)-4-((2S)-(4-(p-nitrobenzyloxycarbonyl) amino-2-hydroxybutyryl)piperazine.

Workup

  1. additionwere added
  2. temperaturewith cooling on an ice bath
  3. customreaction
  4. customfollowed by 2 hours of reaction
  5. customAfter removal of insoluble material from the reaction mixture
  6. filtrationby filtration and subsequent concentration of the filtrate
  7. additiona residue was mixed with ethyl acetate
  8. washwashed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order
  9. dry with materialdried over sodium sulfate
  10. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-31fa6a3cdce649b48cb1b5ac8a7a510a
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

Loading…