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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 272064
ノート
印刷プレビュー

反応式

HRID 272064 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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. 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.

後処理

  1. waitfollowed by an hour
  2. stirring's stirring
  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)

出典と根拠

ORDレコード
ord-36e2dc2c5d40418da4009f07ec7cabaa
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07452908B2

反応ノート

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