Hydrochloric Acid → HCID 11508820, compound

HRID 2242190Notes

Reaction equation

HRID 2242190 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, 1 H), 2.74 (m, 1 H), 2.83 (m, 1 H), 3.09 (m, 1 H), 3.17 (q, 1 H), 3.24 (dd, 1 H), 3.33 (m, 1 H), 3.55 (m, 2 H), 3.64 (m, 1 H), 3.75 (m, 1 H), 3.88 (m, 1 H), 4.52 (m, 1 H), 4.66 (m, 2 H), 7.60 (m, 1 H), 8.06 (t, 1 H), 8.20 (d, 1 H), 8.49 (m, 1 H).

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-fbd78086a214421cb0b44ae164abaa61
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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