Iodine → HCID 67006977, compound

HRID 563194Notes

Reaction equation

HRID 563194 reaction equation
[Si](OC1C=C(C=CC=1)C(NNC(=O)[C@H](NC1C=CC(C#N)=C(Cl)C=1C)[C@H](O[Si](C(C)(C)C)(C)C)C)=O)(C(C)(C)C)(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.[Si:64]([O:71][C@@H:72]([CH3:104])[C@@H:73]([NH:93][C:94]1[CH:101]=[CH:100][C:97]([C:98]#[N:99])=[C:96]([Cl:102])[C:95]=1[CH3:103])[C:74]1[O:75][C:76]([C:79]2[CH:84]=[CH:83][CH:82]=[C:81]([O:85][Si:86]([C:89]([CH3:92])([CH3:91])[CH3:90])([CH3:88])[CH3:87])[CH:80]=2)=[N:77][N:78]=1)([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65]>>[Si:64]([O:71][C@H:72]([CH3:104])[C@@H:73]([NH:93][C:94]1[CH:101]=[CH:100][C:97]([C:98]#[N:99])=[C:96]([Cl:102])[C:95]=1[CH3:103])[C:74]1[O:75][C:76]([C:79]2[CH:84]=[CH:83][CH:82]=[C:81]([O:85][Si:86]([C:89]([CH3:90])([CH3:91])[CH3:92])([CH3:87])[CH3:88])[CH:80]=2)=[N:77][N:78]=1)([C:67]([CH3:68])([CH3:69])[CH3:70])([CH3:65])[CH3:66]

Participants

5

Reactant 4

HCID 807IodineHCID 11776TriphenylphosphineHCID 67005760HCID 67005760, compoundHCID 67006747HCID 67006747, compound2×

Product 1

HCID 67006977HCID 67006977, compound

Procedure

3-(tert-butyldimethylsilyloxy)-N′-((2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)benzohydrazide (intermediate 9b) (362 mg, 0.57 mmol) was cyclized with PS-PPh3 (3.0 mmol/g, 389 mg, 1.2 mmol), I2 (289 mg, 1.1 mmol), and TEA (0.65 mL, 4.7 mmol) as described for the preparation of intermediate 7c. After column chromatography (20% EtOAc/hexanes) the title compound was isolated as a white solid (229 mg, 65%). 1H NMR (500 MHz, CDCl3, δ in ppm) 7.56 (m, 1H), 7.44 (m, 1H), 7.33 (m, 2H), 6.98 (m, 1H), 6.62 (d, J=8.8 Hz, 1H), 5.13 (ad, J=9 Hz, 1H), 4.83 (m, 1H), 4.44 (m, 1H), 2.32 (s, 3H), 1.30 (d, J=6.4 Hz, 3H), 0.99 (s, 9H), 0.93 (s, 9H), 0.21 (s, 6H), 0.13 (s, 3H), 0.11 (s, 3H).

Sources & evidence

ORD record
ord-1851643587c6430d82829b709e7a6fe9
Source dataset
uspto-grants-2011_11
Patent number
US08067448B2

Reaction notes

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