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

HRID 2274700노트

반응식

HRID 2274700 반응식
[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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4125ab5e7fcb4b23977431b3b498bce2
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126981B2

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