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Aniline → (2-Oxo-1-(3-phenylamino-benzyl)-azepan-3-yl]-carbamic acid tert-butyl ester

HRID 1061532
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HRID 1061532 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)([O-])C.[Na+]>C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.O.CC(O)=O.CC(O)=O.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:17]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 3

HCID 6115AnilineHCID 23555228[1-(3-Iodo-benzyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl esterHCID 23676156Sodium t-butoxide

생성물 1

HCID 68950358(2-Oxo-1-(3-phenylamino-benzyl)-azepan-3-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 4

HCID 4144353Palladium (II) acetate촉매
HCID 962
Water
용매
HCID 1140Toluene용매2회
HCID 634876Binap, (A+-)-용매2회

반응 조건

온도
80 °C

실험 절차

In a 100 ml round bottomed flask Binap, (S)-(−)2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (0.210 g, 0.3375 mmol) dissolved in 15 mL toluene was stirred at 80° C. for 1 minute. To the flask cooled to room temperature under inert atmosphere Pd(OAC)2 (0.050 g, 0.225 mmol) was added and the solution was stirred at room temperature for 2 minutes. To the reaction mixture [1-(3-Iodo-benzyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (1.0 g, 2.25 mmol) dissolved in 15 mL toluene, aniline (1.047 g, 11.25 mmol) and Sodium tert-butoxide (0.259 g, 2.70 mmol) were added and the solution was stirred at 80° C. for 18 h. The reaction was cooled to room temperature, diluted with 200 mL of water, and extracted twice with 100 mL of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated to an oil. The oil was purified on flash silica gel column using 10-30% ethyl acetate in hexanes as eluent to yield 0.562 g (61%). MS (ESI) M+H=432.5

후처리

  1. additionwas added
  2. stirringthe solution was stirred at room temperature for 2 minutes
  3. stirringthe solution was stirred at 80° C. for 18 h
  4. temperatureThe reaction was cooled to room temperature
  5. extractionextracted twice with 100 mL of ethyl acetate
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was purified on flash silica gel column
  10. customto yield 0.562 g (61%)

출처 및 근거

ORD 기록
ord-fc646b54ec1247f69da69eb7155ad0a2
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06960576B2

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