Ethanol → HCID 69541968, compound

HRID 989617Notes

Reaction equation

HRID 989617 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:16][CH2:17][C@@H:18]1[O:22][C@H:21]([N:23]2[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@H:20]([OH:32])[CH2:19]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C>N1C=CC=CC=1>[C:1]([O:32][C@@H:20]1[CH2:19][C@H:18]([CH2:17][O:16][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:22][C@@H:21]1[N:23]1[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]1=[O:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 69541953HCID 69541953, compound

Product 1

HCID 69541968HCID 69541968, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.88 mL, 9.28 mmol) was added under argon to a solution of 15 (2.50 g, 7.14 mmol) in dry pyridine (50 mL) and the resulting mixture was stirred at room temperature for 22 h. Then, ethanol was added and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (0-2%) in methylene chloride] to give pure 16 (2.69 g, 96%) as a white foam; mp=68-70° C. (foam); UV (ethanol): λmax=239 nm (ε=15000) 267 nm (ε=8800), λmin=248 nm (ε=5600); 1H NMR (DMSO-d6): δ ppm 11.9 (br s, 1H, NH), 8.1-7.5 (m, 6H, C6H5CO and H-6), 6.10 (d, 1H, H-1′, J1′-2′=4.3 Hz), 5.4 (m, 1H, H-2′), 4.6-4.4 (m, 3H, H-4′, H-5′ and H-5″), 2.6 (m, 1H, H-3′), 2.03 (m, 1H, H-3″), 1.86 (s, 3H, CH3CO); MS (matrix GT): FAB>0 m/z 785 (2M+H)+, 393 (M+H)+, 263 (S)+, 131 (BH2)+, 105 (C6H5CO)+; 43 (CH3CO)+; FAB<0 m/z 391 (M−H)−, 129 (B)−, 121 (C6H5CO2)−, 59 (CH3CO2)−; [α]D20=−81 (c, 0.95 DMSO).

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-fe5cd461f42247e4a654f3d2ad144f28
Source dataset
uspto-grants-2002_10
Patent number
US06458773B1

Reaction notes

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