3,3,3-Triphenylpropionic Acid → N-{(1S)-2-(3-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}amino-3-oxopropyl)amino-1-(2-carbamoylethyl)-2-oxoethyl}-3,3,3-triphenylpropanamide

HRID 394014노트

반응식

HRID 394014 반응식
Cl.[NH2:2][C@@H:3]([CH2:26][CH2:27][C:28]([NH:30]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:29])[C:4]([NH:6][CH2:7][CH2:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:14]1)=[O:10])=[O:5].[C:50]1([C:56]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:57][C:58](O)=[O:59])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(N(CC)C(C)C)(C)C>[CH:20]1([CH2:19][N:15]2[CH2:16][CH2:17][CH2:18][C@H:13]([CH2:12][NH:11][C:9](=[O:10])[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C@@H:3]([NH:2][C:58](=[O:59])[CH2:57][C:56]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH2:26][CH2:27][C:28](=[O:29])[NH2:30])[CH2:14]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

참가 물질

8

반응물 5

HCID 1366963,3,3-Triphenylpropionic AcidHCID 516892Sodium Bicarbonate2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69101269(2S)-2-amino-N5-triphenylmethyl-N1-(3-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}amino-3-oxopropyl)pentanediamide monohydrochloride

생성물 1

HCID 12149945N-{(1S)-2-(3-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}amino-3-oxopropyl)amino-1-(2-carbamoylethyl)-2-oxoethyl}-3,3,3-triphenylpropanamide수율 50.8%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 81531Diisopropylethylamine용매

실험 절차

To a solution of 84 mg of (2S)-2-amino-N5-triphenylmethyl-N1-(3-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}amino-3-oxopropyl)pentanediamide monohydrochloride in 1.5 ml of chloroform, 0.052 ml of N,N-diisopropylethylamine was added at room temperature, followed by an hour's stirring at the same temperature. Then 39 mg of 3,3,3-triphenylpropionic acid, 24 mg of 1-hydroxybenzotriazole monohydrate and 31 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride were added at room temperature by the order stated, followed by 17 hours' stirring at the same temperature. The reaction liquid was rendered weakly basic with saturated aqueous sodium bicarbonate solution, extracted with chloroform and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resultant residue was dissolved in 1 ml of chloroform, and to the solution 1 ml of trifluoroacetic acid was added at room temperature, followed by 20 minutes' stirring at the same temperature. The reaction liquid was rendered weakly basic with saturated aqueous sodium bicarbonate solution, extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified with preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=90/1011) to provide 43 mg of the title compound as a white solid.

후처리

  1. waitfollowed by an hour
  2. stirring' stirring at the same temperature
  3. customThe reaction liquid
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. dissolutionthe resultant residue was dissolved in 1 ml of chloroform
  8. additionto the solution 1 ml of trifluoroacetic acid was added at room temperature
  9. waitfollowed by 20 minutes
  10. stirring' stirring at the same temperature
  11. customThe reaction liquid
  12. extractionextracted with chloroform
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationThe solvent was distilled off under reduced pressure
  15. customthe resultant residue was purified with preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=90/1011)

출처 및 근거

ORD 기록
ord-268aba31ccb0498984af1e3d35017b9e
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809108B1

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