1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-N-benzyl-2-(2-(3-benzylureidooxy)acetamido)-N-(2,2-diethoxyethyl)propanamide

HRID 2362022ノート

反応式

HRID 2362022 の反応式
[CH2:1]([NH:8][C:9](=[O:16])[NH:10][O:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.[NH2:38][C@@H:39]([CH3:58])[C:40]([N:42]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:43][CH:44]([O:48][CH2:49][CH3:50])[O:45][CH2:46][CH3:47])=[O:41]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:51]([N:42]([CH2:43][CH:44]([O:45][CH2:46][CH3:47])[O:48][CH2:49][CH3:50])[C:40](=[O:41])[C@@H:39]([NH:38][C:13](=[O:15])[CH2:12][O:11][NH:10][C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:16])[CH3:58])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 533974882-((3-Benzylureido)oxy)acetic acidHCID 66644890(S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 86658809(S)-N-benzyl-2-(2-(3-benzylureidooxy)acetamido)-N-(2,2-diethoxyethyl)propanamide収率 80%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(3-benzylureidooxy)acetic acid (Compound VI-6) (53.8 mg, 0.24 mmol) and hydroxybenzotriazol (40.5 mg, 0.3 mmol) in dichloromethane (1 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (57.5 mg, 0.3 mmol) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol) and the mixture was stirred at room temperature for 0.5 hr. A solution of (S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamide (Compound IV-19) (58.9 mg, 0.2 mmol) in dichloromethane (1 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 18 hr. The reaction mixture was washed with sat. NaHCO3 aq. (1 ml), water (1 ml) and brine (1 ml). The organic layer was filtered on Celite (1 g) and magnesium sulfate (150 mg). The filtrate was concentrated in vacuo and the residue was purified with PTLC (development solvent: chloroform:methanol=98:2) to obtain the titled compound (60 mg, 80%).

後処理

  1. stirringthe mixture was stirred at room temperature for 18 hr
  2. washThe reaction mixture was washed with sat. NaHCO3 aq. (1 ml), water (1 ml) and brine (1 ml)
  3. filtrationThe organic layer was filtered on Celite (1 g) and magnesium sulfate (150 mg)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified with PTLC (development solvent: chloroform:methanol=98:2)

出典と根拠

ORDレコード
ord-a70a9a2971d04542b8331d57683a09f2
出典データセット
uspto-grants-2014_04
特許番号
US08691819B2

反応ノート

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