Tetrahydrofuran → HCID 178501763, compound

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9](=[O:26])/[CH:10]=[CH:11]/[C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:14]([O:24][CH3:25])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)[C:29]([O-:31])=[O:30].[C:34]([NH:41][C:42](C1C=CNN=1)=[N:43]C(OC(C)(C)C)=O)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[CH3:56]CN(CC)CC.[CH2:63]1[CH2:67]OC[CH2:64]1>>[C:63]([O:31][C:29]([N:41]([C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35])[C:42](=[NH:43])[NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9](=[O:26])/[CH:10]=[CH:11]/[C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:14]([O:24][CH3:25])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1)=[O:30])([CH3:64])([CH3:67])[CH3:56]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 131719422HCID 131719422, compound

HCID 178454276N,N'-bis-BOC-pyrazole carboxamidine

Product 1

HCID 178501763HCID 178501763, compound

Procedure

Benzylic amine salt 112e (0.78 g, 1.7 mmol), N,N'-bis-BOC-pyrazole carboxamidine 122f (0.51 g, 1.5 mmol), and Et3N (0.23 mL, 17 mmol), were stirred in THF (5 mL) at room temperature for 44 h. After evaporation of solvent, the product was isolated by chromatography on silica gel, eluting with 30% to 50% EtOAc in hexane, to yield a yellow solid (0.81 g) following solvent evaporation. IR(KBr) cm-1 3328, 2338, 1760, 1726. 1H NMR(300 MHz, CDCl3): 11.54 (br, 1H), 8.60 (br, 1H), 7.91 (m, 2H), 7.74 (d, 1H, J-16 Hz), 7.54-6.81 (m, 6H), 5.95 (s, 1H), 4.75 (s, 2H), 4 . 72 (d, 2H, J=6 Hz), 3.96 (s, 3H), 3.81 (s, 3H), 1.51 (s, 9H), 1.47 (s, 9H). MS (NH3): 598 (base, M+H).