Hydrochloric Acid → HCID 11508820, compound

HRID 1394134Notes

Reaction equation

HRID 1394134 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24]C)=[O:23])[CH:17]=2)[CH2:10][C@H:9]1[C:27]([N:29]1[CH2:33][CH2:32][S:31][CH2:30]1)=[O:28])=O)(C)(C)C.[OH-].[Na+].Cl>O1CCCC1.C(O)C>[S:31]1[CH2:32][CH2:33][N:29]([C:27]([C@H:9]2[NH:8][CH2:12][C@@H:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]3[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=3)[C:22]([OH:24])=[O:23])[CH2:10]2)=[O:28])[CH2:30]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69242804HCID 69242804, compound

Product 1

HCID 11508820HCID 11508820, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 18A (100 mg) in tetrahydrofuran (0.5 mL) and ethanol (0.5 mL) was added 2 M NaOH (1 mL) and the resulting mixture was stirred at room temperature for 16 hours. The mixture was adjusted to a pH 2-3 by the addition of 1 M HCl, extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (15 mL), dried (Na2SO4), filtered and concentrated to provide a white solid which was processed as described in Example 18 to provide the titled compound as a pale yellow solid. MS (ESI) m/e 364 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 1.82 (m, 1H), 2.74 (m, 1H), 2.83 (m, 1H), 3.09 (m, 1H), 3.17 (q, 1H), 3.24 (dd, 1H), 3.33 (m, 1H), 3.55 (m, 2H), 3.64 (m, 1H), 3.75 (m, 1H), 3.88 (m, 1H), 4.52 (m, 1H), 4.66 (m, 2H), 7.60 (m, 1H), 8.06 (t, 1H), 8.20 (d, 1H), 8.49 (m, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washthe combined organic layers washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a white solid which

Sources & evidence

ORD record
ord-0ae46eb0787346aba66687c06ad1a007
Source dataset
uspto-grants-2008_03
Patent number
US07348346B2

Reaction notes

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