Trifluoroacetic acid → HCID 11756515, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[N:35]1([C:40]2[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=2)[CH:39]=[CH:38][N:37]=[CH:36]1.[B][B][B][B][B][B][B][B][B][B].C(O)(C(F)(F)F)=O>>[CH2:31]([N:30]([CH2:33][CH3:34])[C:28](=[O:29])[C:25]1[CH:26]=[CH:27][C:22]([C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:44][C:43]3[CH:42]=[CH:41][C:40]([N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)=[CH:47][CH:46]=3)[CH:3]=2)[N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:23][CH:24]=1)[CH3:32]Participants
Procedure
Using the same method as for COMPOUND 17 and using INTERMEDIATE 5a (206 mg, 0.44 mmol), 4-(1H-imidazol-1-yl)benzaldehyde (83.6 mg, 0.49 mmol), and decaborane (16.4 mg, 0.13 mmol) afforded COMPOUND 53 (181 mg, 42% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a colourless solid. Purity (HPLC): >99%; Optical purity (Chiral HPLC): >99%; 1H NMR (400 MHz, CD3OD) δ 1.09 (br t, J=6.7 Hz, 3H), 1.21 (br t, J=6.7 Hz, 3H), 2.63 (br s, 4H), 3.15-3.28 (m, 6H), 3.51 (q, J=6.1 Hz, 2H), 4.32 (s, 1H), 4.43 (s, 2H), 6.47-6.52 (m, 1H), 6.71-6.76 (m, 2H), 7.02 (t, J=8.0 Hz, 1H), 7.26 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.6 Hz, 2H), 7.64 (d, J=8.6 Hz, 2H), 7.76 (s, 1H), 8.05 (s, 1H), 9.44 (s, 1H). Found: C, 51.44; H, 4.89; N, 9.63. C32H38N6O×1.2 H2O×3.0 CF3COOH has C, 51.49; H, 4.94, N, 9.48%. [α]D17=−2.1 deg [c 0.872, MeOH].
Sources & evidence
- ORD record
- ord-1be2dbee2834409590c40f178cbcce9e
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241764B2
Reaction notes
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