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tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate → N-(2-{3-({(3R)-1-(tert-butoxycarbonyl)-3-piperidyl}methyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide

HRID 394009
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HRID 394009 반응식
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[C:16]1([C:22]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:23][C:24]([NH:26][CH2:27][C:28]([NH:30][CH2:31][CH2:32][C:33](O)=[O:34])=[O:29])=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:12]([O:11][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:3]([CH2:2][NH:1][C:33](=[O:34])[CH2:32][CH2:31][NH:30][C:28](=[O:29])[CH2:27][NH:26][C:24](=[O:25])[CH2:23][C:22]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:4]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]
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참가 물질

8

반응물 4

HCID 1502023tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 110045083-(2-{(3,3,3-Triphenylpropanoyl)amino}acetylamino)propionic acid

생성물 1

HCID 11734836
N-(2-{3-({(3R)-1-(tert-butoxycarbonyl)-3-piperidyl}methyl)amino-3-oxopropyl}amino-2-oxoethyl)-3,3,3-triphenylpropanamide
수율 88%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 0.55 g of (3R)-3-aminomethyl-1-(tert-butoxycarbonyl)piperidine and 1.1 g of 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionic acid in 10 ml of N,N-dimethylformamide, 0.52 g of 1-hydroxybenzotriazole monohydrate and 0.75 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride were successively added at room temperature, and stirred for 2 hours at the same temperature. Then 2.0 ml of triethylamine and 10 ml of chloroform were added at room temperature, followed by an hour's stirring at the same temperature. The reaction liquid was distilled off under reduced pressure, diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by means of silica gel column chromatography (eluting solvent: chloroform/methanol=19/1) to provide 1.41 g of the title compound.

후처리

  1. waitfollowed by an hour
  2. stirring's stirring at the same temperature
  3. customThe reaction liquid
  4. distillationwas distilled off under reduced pressure
  5. additiondiluted with ethyl acetate
  6. washwashed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by means of silica gel column chromatography (eluting solvent: chloroform/methanol=19/1)

출처 및 근거

ORD 기록
ord-45c3454b2e444ec5baabed92b3320496
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06809108B1

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