Water → HCID 67224085, 화합물

HRID 1963976노트

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HRID 1963976 반응식
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.[Br:58][C:59]1[CH:68]=[CH:67][C:62]([C:63](=[N:65]O)[NH2:64])=[CH:61][CH:60]=1>CN(C)C=O>[Br:58][C:59]1[CH:68]=[CH:67][C:62]([C:63]2[N:65]=[C:10]([C@@H:9]3[CH2:13][CH2:14][CH2:15][N:8]3[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[O:12][N:64]=2)=[CH:61][CH:60]=1

참가 물질

8

반응물 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27568384-Bromo-N-hydroxybenzimidamide

생성물 1

HCID 67224085HCID 67224085, 화합물수율 54.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-Boc-L-proline (2.5 g, 11.6 mmol) in N,N-dimethylformamide (18 mL), O-(Benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (TBTU, 3.73 g, 11.6 mmol), HOBt.H2O (0.36 g, 2.32 mmol) and DIPEA (10.2 ml, 58.1 mmol) were added. After the reaction mixture was stirred at room temperature for 5 minutes, 4-Bromo-N′-hydroxybenzimidamide 15 (2.5 g, 11.6 mmol) was added. The mixture was then stirred at 110° C. for 2.5 hours. After cooled to room temperature, the resulting mixture was extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated to yield a crude yellow liquid, which was purified with chromatography (ethyl acetate: n-hexane=1:10) to give the desired product 16a (2.5 g).

후처리

  1. stirringThe mixture was then stirred at 110° C. for 2.5 hours
  2. temperatureAfter cooled to room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude yellow liquid, which
  8. customwas purified with chromatography (ethyl acetate: n-hexane=1:10)

출처 및 근거

ORD 기록
ord-f8d418972cb8425887c7bd47c64c41f3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415482B2

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