HCID 15870455, compound → HCID 15870457, compound

HRID 609537Notes

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 δ 8.92 (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-90e7b13da2c544a5865bddefa72602f9
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998203

Reaction notes

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