Iodine → HCID 67006036, 화합물

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C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.[Si:22]([O:29][C:30]1[CH:31]=[C:32]([CH:61]=[CH:62][C:63]=1[F:64])[C:33]([NH:35][NH:36][C:37](=[O:60])[C@H:38]([NH:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[C:52](Cl)[C:51]=1C)[C@@H:39]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH3:40])=O)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].[CH2:65]([Cl:67])Cl>>[Si:42]([O:41][C@H:39]([CH3:40])[C@@H:38]([NH:49][C:50]1[CH:51]=[CH:52][C:53]([C:56]#[N:57])=[C:65]([Cl:67])[C:55]=1[CH3:54])[C:37]1[O:60][C:33]([C:32]2[CH:61]=[CH:62][C:63]([F:64])=[C:30]([O:29][Si:22]([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:23])[CH3:24])[CH:31]=2)=[N:35][N:36]=1)([C:45]([CH3:48])([CH3:46])[CH3:47])([CH3:44])[CH3:43]

참가 물질

반응물 4

HCID 807Iodine

HCID 6344Dichloromethane

HCID 11776Triphenylphosphine

HCID 67006002HCID 67006002, 화합물

생성물 1

HCID 67006036HCID 67006036, 화합물

실험 절차

Triphenylphosphine (1.0 g, 3.85 mmol) was dissolved in 25 mL of DCM followed by addition of I2 (977 mg, 3.85 mmol) and TEA (779 mg, 7.70 mmol) at 0° C. 3-(tert-butyldimethylsilyloxy)-N′-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)-4-fluorobenzohydrazide (1.25 g, 1.93 mmol) in 35 mL DOA was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stir. The temperature was allowed to rise to room temperature and stirred for additional 10 min. The reaction was quenched with 100 mL saturated sodium thiosulfate and extracted with EtOAc. The crude mixture was chromatographed to give the product (1.10 g). 1H NMR (400 MHz, DMSO-d6, δ in ppm): 7.71 (m, 1H), 7.70 (d, J=9 Hz, 1H), 7.65 (m, 1H), 7.03 (d, J=9 Hz, 1H), 6.53 (d, J=9 Hz, 1H), 5.15 (d, J=9 Hz, 1H), 4.80 (m, 1H), 2.44 (s, 3H), 1.51 (d, J=6 Hz, 3H), 1.13 (s, 9H), 0.83 (s, 9H), 0.36 (s, 6H), 0.19 (s, 3H), 0.00 (s, 3H).