3-Oxetanone → HCID 58204201, compound

HRID 1849353Notes

Reaction equation

HRID 1849353 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([NH2:28])[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1.[O:29]1[CH2:32][C:31](=O)[CH2:30]1>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([NH:28][CH:31]5[CH2:32][O:29][CH2:30]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1

Participants

4

Reactant 2

HCID 150242543-OxetanoneHCID 58204142HCID 58204142, compound

Product 1

HCID 58204201HCID 58204201, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Compound 134 (200 mg, 0.5 mmol) was dissolved in THF, and oxetan-3-one (252 mg, 0.35 mmol) was added at 0° C. The mixture was warmed to 80° C. and stirred for 0.5 h at this temperature. It was cooled to 0° C., NaBH(CN)3 (67 mg, 0.6 mmol) was added. Then the mixture was warmed to 80° C. and stirred for further 0.5 h at this temperature. The reaction mixture was filtered to gather the solution. Then water was added into the solution. It was extracted by DCM (20 mL×3). The combined organics were dried over Na2SO4, concentrated in vacuo, and separated by prep TLC (EtOAc/hexanes=4:1) to give 434 (115 mg, yield: 50%). 1H NMR (DMSO-d6, 400 MHz): δ9.42 (s, 1 H), 8.42 (s, 1 H), 8.00-7.49 (m, 4 H), 7.12 (s, 1 H), 7.04 (d, J=9.6 Hz, 1H), 4.85-4.83 (m, 1 H), 4.58-4.38 (m, 4 H), 3.65 (t, J=6.4 Hz, 2 H), 2. 93 (t, J=6.4 Hz, 2 H). LC-MS (ESI): m/z=454 [M+H]+

Workup

  1. temperatureIt was cooled to 0° C.
  2. temperatureThen the mixture was warmed to 80° C.
  3. stirringstirred for further 0.5 h at this temperature
  4. filtrationThe reaction mixture was filtered
  5. additionThen water was added into the solution
  6. extractionIt was extracted by DCM (20 mL×3)
  7. dry with materialThe combined organics were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customseparated by prep TLC (EtOAc/hexanes=4:1)

Sources & evidence

ORD record
ord-aba5feec918b4f41a1cfbdf57e4463e4
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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