Iodine → HCID 67005994, compound

HRID 470780Notes

Reaction equation

[Si](O[C@H](C)[C@@H](NC1C=CC(C#N)=C(Cl)C=1C)C1OC(C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2)=NN=1)(C(C)(C)C)(C)C.[Si:42]([O:49][C:50]1[CH:83]=[CH:82][C:53]([C:54]([NH:56][NH:57][C:58](=[O:81])[C@H:59]([NH:70][C:71]2[CH:76]=[CH:75][C:74]([C:77]#[N:78])=[C:73]([Cl:79])[C:72]=2[CH3:80])[C@@H:60]([O:62][Si:63]([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64])[CH3:61])=O)=[CH:52][C:51]=1[F:84])([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II>>[Si:63]([O:62][C@@H:60]([CH3:61])[C@@H:59]([NH:70][C:71]1[CH:76]=[CH:75][C:74]([C:77]#[N:78])=[C:73]([Cl:79])[C:72]=1[CH3:80])[C:58]1[O:81][C:54]([C:53]2[CH:82]=[CH:83][C:50]([O:49][Si:42]([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:43])[CH3:44])=[C:51]([F:84])[CH:52]=2)=[N:56][N:57]=1)([C:66]([CH3:69])([CH3:67])[CH3:68])([CH3:65])[CH3:64]

Participants

Reactant 4

HCID 807Iodine

HCID 11776Triphenylphosphine

HCID 67005983HCID 67005983, compound

HCID 670065564-((1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-(tert-butyldimethylsilyloxy)phenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile

Product 1

HCID 67005994HCID 67005994, compound

Procedure

Intermediate 29e was prepared by a procedure analogous to that used for the preparation of intermediate 10c by cyclization of 4-(tert-butyldimethylsilyloxy)-N′-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)-3-fluoro benzohydrazide (640 mg, 0.99 mmol) with PS-PPh3 (3.0 mmol/g, 661 mg, 1.98 mmol), I2 (502 mg, 1.98 mmol), and TEA (1.4 mL, 10 mmol). After column chromatography (25% EtOAc/hexanes) the title compound was isolated as a white solid (131 mg, 21%). 1H NMR (400 MHz, CDCl3, δ in ppm) 7.65 (m, 1H), 7.59 (m, 1H), 7.32 (d, J=8.6 Hz, 1H), 6.9 (t, J=8.3 Hz, 1H), 6.45 (d, J=8.8 Hz, 1H), 5.35 (d, J=8.6 Hz, 1H), 4.77 (dd, J=1.9, 8.7 Hz, 1H), 4.51 (m, 1H), 2.36 (s, 3H), 1.40 (d, J=6.1 Hz, 3H), 0.99 (s, 9H), 0.86 (s, 9H), 0.21 (s, 6H), 0.06 (s, 3H), −0.20 (s, 3H).

Workup

customIntermediate 29e was prepared by a procedure analogous to

Sources & evidence

ORD record: ord-c810497eb92f41c9a229d8b8a7aa0b29
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629167B2

Reaction notes

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