Hydrochloric Acid → HCID 21084006, compound

HRID 347922Notes

Reaction equation

HRID 347922 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:24](C(OCC)=O)[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.Cl>O1CCOCC1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:24][S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21084060HCID 21084060, compound

Product 1

HCID 21084006HCID 21084006, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound of Example 92 (91 mg, 0.18 mmol) was dissolved in dioxane (1 mL) and 4M HCl(aq) (1 mL) added and the mixture heated at reflux for 48 h. The reaction was partitioned between 2M NaOH(aq) and THF and the combined THF layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0–10% MeOH in EtOAc) to give the title compound as an off-white solid (73 mg, 94%). δH (CDCl3) 7.74 (1H, d, J 9.6 Hz), 7.33–7.28 (7H, m), 7.05–7.01 (2H, m), 6.75 (1H, s), 6.58 (1H, d, J 9.6 Hz), 4.12 (2H, t, J 5.7 Hz), 3.76–3.67 (4H), m), 2.78 (2H, t, J 5.7 Hz), 2.56–2.52 (4H, m). LCMS (ES+) RT 2.46 minutes, 433 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 48 h
  3. customThe reaction was partitioned between 2M NaOH(aq) and THF
  4. dry with materialthe combined THF layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 0–10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-8ddb5952add144a5841df3e9b301c950
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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