Tetrahydrofuran → HCID 90410776, compound

HRID 1754618Notes

Reaction equation

HRID 1754618 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C@H:9]([C@H:12]([OH:14])[CH3:13])[CH2:10][OH:11])[C:4](=[O:15])[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C[O:37][CH2:36][CH2:35]1>>[C:36]([NH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C@H:9]([C@H:12]([OH:14])[CH3:13])[CH2:10][OH:11])[C:4](=[O:15])[N:3]=1)(=[O:37])[CH3:35]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 90411297HCID 90411297, compound

Product 1

HCID 90410776HCID 90410776, compoundYield 72%

Procedure

To a solution of 45 (1.3 g, 2.7 mmol) in 38 ml of THF was added 2.3 ml of 1M TBAF in THF. The reaction was stirred for 24 hrs, concentrated and chromatographed on silica eluting with, first, 10% MeOH in dichloromethane and, second, with 15% MeOH in dichloromethane. Concentration of the pure product fractions afforded 0.5 g (72%) of 46 as white amorphous solid. 1H NMR (DMSO-d6): δ10.81 (s, 1H), 7.98 (d, J=7 Hz, 1H), 7.12 (d, J=7 Hz, 1H), 4.58 (d, J=5 Hz, 1H), 4.48 (t, J=5 Hz, 1H), 3.82 (d, J=7 Hz, 2H), 3.67 (m, 1H), 3.46 (m, 1H), 3.38 (m, 1H), 2.09 (s, 3H), 1.89 (m, 1H), 1.09 (d, J=6 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica eluting with, first, 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-152bca398437428d944b3f7e571aadd0
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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