Dichloromethane → HCID 67006478, compound

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:20]([O:27][C:28]1[CH:29]=[C:30]([CH:59]=[CH:60][C:61]=1[F:62])[C:31]([NH:33][NH:34][C:35](=[O:58])[C@H:36]([NH:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]#[N:55])=[C:50](Cl)[C:49]=1C)[C@@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])=O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[CH2:63]([Cl:65])Cl>>[Si:40]([O:39][C@@H:37]([CH3:38])[C@@H:36]([NH:47][C:48]1[CH:49]=[CH:50][C:51]([C:54]#[N:55])=[C:63]([Cl:65])[C:53]=1[CH3:52])[C:35]1[O:58][C:31]([C:30]2[CH:59]=[CH:60][C:61]([F:62])=[C:28]([O:27][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH:29]=2)=[N:33][N:34]=1)([C:43]([CH3:46])([CH3:44])[CH3:45])([CH3:42])[CH3:41]

Participants

Reactant 3

HCID 6344Dichloromethane2×

HCID 11776Triphenylphosphine

HCID 67006002HCID 67006002, compound

Product 1

HCID 67006478HCID 67006478, compound

Procedure

Triphenylphosphine (331 mg, 1.26 mmol) was dissolved in 25 mL of DCM followed by addition of 12 (321 mg, 1.26 mmol) and TEA (256 mg, 2.53 mmol) at 0° C. 3-(tert-butyldimethylsilyloxy)-N′-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)-4-fluorobenzohydrazide (410 mg, 0.631 mmol) in 15 mL DCM was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred. The temperature was allowed to rise to room temperature and stirred for additional 10 min. The reaction was quenched with 50 mL saturated sodium thiosulfate and extracted with EtOAc. The crude mixture was chromatographed to give the product (400 mg). 1H NMR (500 MHz, CDCl3, δ in ppm): 7.69 (m, 3H), 7.54 (d, J=9 Hz, 1H), 7.35 (t, J=9 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 5.56 (d, J=9 Hz, 1H), 4.99 (m, 1H), 4.74 (m, 1H), 2.37 (s, 3H), 1.62 (d, J=6 Hz, 3H), 1.20 (s, 9H), 1.06 (s, 9H), 0.40 (s, 6H), 0.27 (s, 3H), 0.00 (s, 3H).