Diethyl Ether → HCID 20607403, compound

HRID 431085Notes

Reaction equation

HRID 431085 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 12112030HCID 12112030, compound

Product 1

HCID 20607403HCID 20607403, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 30A (60 mg, 0.303 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (60 mg, 0.318 mmol) and stirred for 5 minutes. Then ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. The residue was then dried under vacuum to provide 30 as a white solid. mp 107-109° C.; MS (APCI+) m/e 199 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.40 (s, 3H), 2.92 (s, 6H), 3.90 (m, 1H), 4.27 (dd, J=8, 11 Hz, 1H), 4.40 (dd, J=4, 12 Hz, 1H), 7.10 (m, 1H), 7.36-7.39 (m, 2H), 7.65 (m, 1H), 7.68-7.72 (m, 2H), 7.90 (dd, J=1, 3 Hz, 1H); Analysis calculated for C10H15N2FO.C7H8O3S: C, 55.12; H, 6.25; N, 7.56; Found: C, 54.88; H, 6.17; N, 7.29; [α]25D=−10° (c=0.30, MeOH).

Workup

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

Sources & evidence

ORD record
ord-ea56e5f42c024aba8554dfa3d2ef00ad
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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