Diethyl Ether → HCID 20607435, compound

HRID 431080Notes

Reaction equation

HRID 431080 reaction equation
[CH3:1][N:2]([CH3:14])[C@@H:3]([CH3:13])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([F:12])=[N:10][CH:11]=1.O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(OCC)C>C(OCC)(=O)C>[C:16]1([CH3:26])[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[CH3:1][N:2]([CH3:14])[C@@H:3]([CH3:13])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([F:12])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 12112022HCID 12112022, compound

Product 1

HCID 20607435HCID 20607435, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5A (88 mg, 0.444 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (89 mg, 0.467 mmol) and stirred for 5 minutes. Ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. It was then dried under vacuum to provide 5 as a white solid. mp 81-83° C.; MS (CI/NH3) m/e 199 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.40 (s, 3H), 2.91 (s, 6H), 3.90 (m, 1H), 4.26 (dd, J=8, 11 Hz, 1H), 4.49 (dd, J=4, 11 Hz, 1H), 7.10 (dd, J=2, 9 Hz, 1H), 7.38 (d, J=8 Hz, 2H), 7.65 (m, 1H), 7.70 (d, J=9 Hz, 2H), 8.90 (dd, J=1, 3 Hz, 1H); Analysis calculated for C10H15N2FO.1.1C7H8O3S: C, 54.84; H, 6.19; N, 7.23; Found: C, 54.48; H, 6.35; N, 7.20; [α]25D=+5.1° (c=0.85, MeOH).

Workup

  1. stirringstirred for an additional 5 minutes
  2. customThe ether was decanted
  3. customIt was then dried under vacuum

Sources & evidence

ORD record
ord-b361176fd8394fdf974a30fdd835e542
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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