HCID 15870455, compound → HCID 15870457, compound

HRID 1355342Notes

Reaction equation

[N+](C1C=CC(S(OC[C@H]2O[C@@H](N3C4N=CN=C(NC(=O)C5C=CC=CC=5)C=4N=C3)[C@H](OC)[C@@H]2O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1)([O-])=O.Cl[CH2:59][C@H:60]1[O:64][C@@H:63]([N:65]2[C:82]3[N:81]=[CH:80][N:79]=[C:69]([NH:70][C:71](=[O:78])[C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)[C:68]=3[N:67]=[CH:66]2)[C@H:62]([O:83][CH3:84])[C@@H:61]1[O:85][Si:86]([C:99]([CH3:102])([CH3:101])[CH3:100])([C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1)[C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1.[Li][N:104]=[N+:105]=[N-:106]>CS(C)=O>[N:104]([CH2:59][C@H:60]1[O:64][C@@H:63]([N:65]2[C:82]3[N:81]=[CH:80][N:79]=[C:69]([NH:70][C:71](=[O:78])[C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)[C:68]=3[N:67]=[CH:66]2)[C@H:62]([O:83][CH3:84])[C@@H:61]1[O:85][Si:86]([C:99]([CH3:102])([CH3:101])[CH3:100])([C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1)[C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1)=[N+:105]=[N-:106]

Participants

Conditions

Temperature: 80 °C

Procedure

(FIG. 8C) The above mixture of 14 and 15 (3.9 g) was dissolved in dry DMSO (30 mL) and LiN3 (1.18 g, 24 mmol) was added. The reaction mixture was stirred at 80° C. overnight, then concentrated in vacuo (oil pump). After standard work up and column chromatography using 1-2% gradient MeOH in CH2Cl2 16 was obtained as a colorless foam (2.55 g), 1H NMR δ8.92 (br s, 1H, NH), 8.72 (s, 1H, H2), 8.15 (s, 1H, H8), 8.02-7.36 (m, 15H, 3×Ph), 6.14 (d, J1′,2′=3.4, 1H, H1′), 4.44 (app t, J3′,4′=5.1, 1H, H3′), 4.27 (m, 1H, H4′), 4.01 (app t, J2′,1′=3.4, J2′,3′=4.9, 1H, H2′), 3.53 (dd, J5′,4′=3.2, J5′,5″=13.3, 1H, H5′), 3.37 (dd, J5″,4′=4.5, J5″,5′=13.3, 1H, H5″), 3.29 (s, 3H, OMe), 1.13 (s, 9H, t-Bu).

Workup

concentrationconcentrated in vacuo (oil pump)

Sources & evidence

ORD record: ord-dc9d0a54acfe41b2a4c938d377ddb1bc
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586238B1

Reaction notes

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