1-Hydroxybenzotriazole → t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

HRID 1291027노트

반응식

HRID 1291027 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=O)[O:9][C:6]2=[N:7][CH:8]=1)#[N:2].[NH2:15][C:16]1[CH:30]=[CH:29][C:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:29][CH:30]=3)=[O:14])[O:9][C:6]2=[N:7][CH:8]=1)#[N:2]

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108452775-Cyanofuro[2,3-b]pyridine-2-carboxylic acidHCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

생성물 1

HCID 10500772t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-Cyanofuro[2,3-b]pyridine-2-carboxylic acid (108 mg, 0.574 mmol) and t-butyl 4-aminophenoxyacetate (141 mg, 0.632 mmol) were dissolved in N,N-dimethylformamide (10 ml) and 1-hydroxy-1H-benzotriazole (85.3 mg, 0.632 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.632 mmol) were added. The mixture was stirred at room temperature for 14 hours. Water (100 ml) was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. Low boiling matters were distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to quantitatively give 232 mg of t-butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate as a pale-yellow solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationwere distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to quantitatively give 232 mg of t-butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate as a pale-yellow solid

출처 및 근거

ORD 기록
ord-118095f4faea4a35b206cfcfc0c858de
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753670

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