Triphenylphosphine → HCID 67006977, compound

HRID 1254643Notes

Reaction equation

HRID 1254643 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.[Si:62]([O:69][C@@H:70]([CH3:102])[C@@H:71]([NH:91][C:92]1[CH:99]=[CH:98][C:95]([C:96]#[N:97])=[C:94]([Cl:100])[C:93]=1[CH3:101])[C:72]1[O:73][C:74]([C:77]2[CH:82]=[CH:81][CH:80]=[C:79]([O:83][Si:84]([C:87]([CH3:90])([CH3:89])[CH3:88])([CH3:86])[CH3:85])[CH:78]=2)=[N:75][N:76]=1)([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:64])[CH3:63]>>[Si:62]([O:69][C@H:70]([CH3:102])[C@@H:71]([NH:91][C:92]1[CH:99]=[CH:98][C:95]([C:96]#[N:97])=[C:94]([Cl:100])[C:93]=1[CH3:101])[C:72]1[O:73][C:74]([C:77]2[CH:82]=[CH:81][CH:80]=[C:79]([O:83][Si:84]([C:87]([CH3:88])([CH3:89])[CH3:90])([CH3:85])[CH3:86])[CH:78]=2)=[N:75][N:76]=1)([C:65]([CH3:66])([CH3:67])[CH3:68])([CH3:63])[CH3:64]

Participants

4

Reactant 3

HCID 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), 12 (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-6869f65177934e9e81dfae38c00db888
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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