Hydrochloric Acid → HCID 45275163, compound

HRID 1667189Notes

Reaction equation

HRID 1667189 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:42])[CH2:21][N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:23]2=[O:41])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.O1CCOCC1>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:42])[CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:23]2=[O:41])[CH2:16][CH2:15]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67359031HCID 67359031, compound

Product 1

HCID 45275163HCID 45275163, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The compound from Example 101D (0.24 g, 0.42 mmol) was dissolved in methanol and treated with 4 N HCl in dioxane at ambient temperature for 2 hours. The reaction mixture was concentrated and then partitioned in 1 N NaOH/methylene chloride. The organic layer was dried over MgSO4, concentrated in vacuo and chromatographed, eluting with 5% MeOH/methylene chloride to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.15-7.48 (m, 15H), 4.30-4.44 (m, 3H), 3.91-4.27 (m, 2H), 3.33-3.55 (m, 4H), 2.80-3.07 (m, 4H), 2.23-2.34 (m, 4H); MS (ESI+) m/z 469 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned in 1 N NaOH/methylene chloride
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customchromatographed
  6. washeluting with 5% MeOH/methylene chloride

Sources & evidence

ORD record
ord-4b88a9dae93f4f6ba9ece6215eec56df
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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