1-Piperazinecarboxylic acid, ethyl ester → HCID 131727694, compound

HRID 1157360Notes

Reaction equation

HRID 1157360 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:17]2[CH:22]=[C:21]([I:23])[C:20]([O-:24])=[C:19]([I:25])[CH:18]=2)=[C:8]2[CH:14]=[C:13]([I:15])[C:11](=[O:12])[C:10]([I:16])=[CH:9]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+].[N+:31]([C:34]1[CH:35]=[C:36]([CH:43]=[CH:44][CH:45]=1)[CH2:37][C@@H:38]([C:40]([OH:42])=O)[NH2:39])([O-:33])=[O:32].[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)=[O:50])[CH3:47].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:1]1[CH:6]=[C:5]([C:7]([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O-:12])=[C:13]([I:15])[CH:14]=2)=[C:17]2[CH:18]=[C:19]([I:25])[C:20](=[O:24])[C:21]([I:23])=[CH:22]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+:29].[CH2:46]([O:48][C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:40](=[O:42])[C@H:38]([CH2:37][C:36]2[CH:43]=[CH:44][CH:45]=[C:34]([N+:31]([O-:33])=[O:32])[CH:35]=2)[NH2:39])[CH2:55][CH2:56]1)=[O:50])[CH3:47]

Participants

6

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131727696HCID 131727696, compound

Product 1

HCID 131727694HCID 131727694, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

TIPPS-3-nitro-(L)-phenylalanine (210 g; 0.44 mmol; 76% purity), ethyloxycarbonylpiperazine (69.7 g; 0.44 mmol) and 1-hydroxybenzotriazole (101 g; 660 mmol) were dissolved in 650 ml of DMF and cooled to 10° C. A solution of dicyclohexylcarbodiimide (100 g; 0.484 mmol) in 216 ml of DMF was added dropwise over a period of 2 h and the reaction solution was stirred at RT overnight. After evaporating the solvent, the residue was dissolved in 436 ml of MTBE, the precipitate was filtered off, and the organic solution was extracted in each case 2× with 5% KHSO4, 5% NaHCO3 and distilled water. The solvent was evaporated under vacuum, toluene was added and then evaporated in a rotary evaporator and the product was dried under vacuum.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in 436 ml of MTBE
  3. filtrationthe precipitate was filtered off
  4. extractionthe organic solution was extracted in each case 2× with 5% KHSO4, 5% NaHCO3
  5. distillationdistilled water
  6. customThe solvent was evaporated under vacuum, toluene
  7. additionwas added
  8. customevaporated in a rotary evaporator
  9. customthe product was dried under vacuum

Sources & evidence

ORD record
ord-5f401a95b1c3486fa8db25cbad9d780f
Source dataset
uspto-grants-2010_10
Patent number
US07807681B2

Reaction notes

Loading…