Dichloromethane → HCID 67006036, compound

HRID 1254701Notes

Reaction equation

HRID 1254701 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

4

Reactant 3

HCID 6344Dichloromethane2×HCID 11776TriphenylphosphineHCID 67006002HCID 67006002, compound

Product 1

HCID 67006036HCID 67006036, compound

Procedure

Triphenylphosphine (1.0 g, 3.85 mmol) was dissolved in 25 mL of DCM followed by addition of 12 (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 DCM 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).

Workup

  1. customto rise to room temperature
  2. stirringstirred for additional 10 min
  3. customThe reaction was quenched with 100 mL saturated sodium thiosulfate
  4. extractionextracted with EtOAc
  5. customThe crude mixture was chromatographed

Sources & evidence

ORD record
ord-fd9afd79400d4bd884f3f614d64d2000
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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