Ethanol → HCID 69541968, compound

HRID 2186668Notes

Reaction equation

HRID 2186668 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 mnixture 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): λmax239 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-5a1e6551206243bcb5fdd436c156d816
Source dataset
uspto-grants-2002_06
Patent number
US06407077B1

Reaction notes

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