1-Methylpiperazine → HCID 18639812, compound

HRID 1031256Notes

Reaction equation

HRID 1031256 reaction equation
[C:1]([S:4][CH:5]([CH:10]([C:15]([NH:17][C@H:18]([C:28]([NH:30][CH3:31])=[O:29])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][C:7](O)=[O:8])(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>ClCCl>[C:1]([S:4][CH:5]([CH:10]([C:15]([NH:17][C@H:18]([C:28]([NH:30][CH3:31])=[O:29])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])[CH2:6][C:7]([N:46]1[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 18639816HCID 18639816, compound

Product 1

HCID 18639812HCID 18639812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 3-acetylmercapto-6-methyl-4-[[[1-(S)-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]-carbonyl]heptanoic acid (E5, Isomer A; 226 mg, 0.5 mmol), N,N1 -dicyclohexylcarbodiimide (103 mg, 0.5 mmol), 1-hydroxybenzotriazole (76 mg, 0.5 mmol) and N-methylpiperazine (0.05 ml, 0.5 mmol) in dichloromethane (8 ml) was stirred at 5° C. for 1 h, then at room temperature overnight. After cooling, the precipitated solid was filtered off. The solution was diluted with dichloromethane and extracted with 0.25 M citric acid. The extracts were washed with dichloromethane then basified with 10% sodium carbonate, and extracted with ether. The ether extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. Trituration of the oily residue with ether, followed by recrystallisation of the resulting solid from ethyl acetate/hexane gave the title compound as a single isomer (Isomer A), 98 mg (37%) mp 133°-138° C. (Found: C,60.48; H,8.15; N,10.40. C27H42N404S requires C,60.65; H,7.92; N,10.48%).

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered off
  5. additionThe solution was diluted with dichloromethane
  6. extractionextracted with 0.25 M citric acid
  7. washThe extracts were washed with dichloromethane
  8. extractionextracted with ether
  9. washThe ether extracts were washed with brine
  10. dry with materialdried (Na2SO4)
  11. customevaporated in vacuo
  12. customTrituration of the oily residue with ether, followed by recrystallisation of the resulting solid from ethyl acetate/hexane

Sources & evidence

ORD record
ord-45b8bbe1159745cb87d8ccdb1456ae74
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Reaction notes

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