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Ethylmorpholine → 3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide

HRID 2353090
ノート
印刷プレビュー

反応式

HRID 2353090 の反応式
C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=O)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[NH2:36][CH:37]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=1)[C:38]([N:40]([CH2:44][CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48])[CH:41]([CH3:43])[CH3:42])=[O:39]>CN(C=O)C.C(Cl)CCl>[Cl:59][C:56]1[CH:55]=[CH:54][C:53]([CH2:52][CH:37]([NH:36][C:33](=[O:35])[CH2:32][CH2:31][NH:30][S:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=2)(=[O:28])=[O:29])[C:38]([N:40]([CH2:44][CH:45]([O:46][CH2:47][CH3:48])[O:49][CH2:50][CH3:51])[CH:41]([CH3:42])[CH3:43])=[O:39])=[CH:58][CH:57]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7573773-(4-Methoxy-benzenesulfonylamino)-propionic acidHCID 673416462-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

生成物 1

HCID 684528403-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide

試薬・触媒・溶媒

2
HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

52 mg of EDC, 45 mg of HOBt and 100 μl of N-ethylmorpholine are added to a solution of 124 mg of 3-(4-methoxybenzenesulfonylamino)propionic acid in 1 ml of DMF. A solution of 100 mg of 2-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide in 1 ml of DMF is added dropwise thereto, and the mixture is left to stir for 12 h. The reaction solution is filtered, mixed with ethyl acetate and then extracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution. Drying of the organic phase with Chromabond XTR is followed by concentration under reduced pressure, and the residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=598.16 (calculated); measured value (M-C2H6O+H)+: 552.1

後処理

  1. waitthe mixture is left
  2. filtrationThe reaction solution is filtered
  3. additionmixed with ethyl acetate
  4. extractionextracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution
  5. customDrying of the organic phase with Chromabond XTR
  6. concentrationis followed by concentration under reduced pressure
  7. customthe residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

出典と根拠

ORDレコード
ord-bde0449d2e654c228fcdad4114da4c0f
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07750005B2

反応ノート

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