Tetrahydrofuran → HCID 178501763, compound

HRID 259783Notes

Reaction equation

HRID 259783 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

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 131719422HCID 131719422, compoundHCID 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).

Workup

  1. customAfter evaporation of solvent
  2. customthe product was isolated by chromatography on silica gel
  3. washeluting with 30% to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-5898819c550840749421896727d8ed99
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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