Hydrochloric Acid → HCID 9870752, compound

HRID 1861687Notes

Reaction equation

HRID 1861687 reaction equation
O[Li].O.[Cl:4][C:5]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:6]=1[CH2:7][O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][CH:14]([C:19]([NH:21][C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[O:30][CH3:31])=[O:20])[C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=1.Cl>C1COCC1.O>[Cl:4][C:5]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:6]=1[CH2:7][O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][CH:14]([C:19]([NH:21][C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[O:30][CH3:31])=[O:20])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 12967489HCID 12967489, compound

Product 1

HCID 9870752HCID 9870752, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (120 mg, 2.9 mmol) was added to a solution of the compound of Example 1 (0.98 g, 1.9 mmol) in THF (10 ml) and water (5 ml) and the reaction stirred at room temperature for 1.5 h, then acidified to pH1 with 10% hydrochloric acid and extracted with DCM (2×25 ml). The combined organic layers were dried (MgSO4) and the solvent evaporated in vacuo to give a white foam that was triturated with DCM/Et2O to give the title compound as a white solid (0.52 g, 54%). δH (DMSO d6) 9.09 (1H, br s, NH), 7.58-7.44 (3H, m, Ar—H), 6.98 (2H, d, J 8.4 Hz, Ar—H), 6.65 (2H, d, J 8.4 Hz, Ar—H), 5.20 (2H, s, CH2OAr), 3.69 (6H, s, OMe), 3.69 (1H, m, CHCH2) and 3.05 (2H, m, CHCH2). m/z (ESI, 60V) 504, 506 (MH+).

Workup

  1. extractionextracted with DCM (2×25 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customthe solvent evaporated in vacuo
  4. customto give a white foam that
  5. customwas triturated with DCM/Et2O

Sources & evidence

ORD record
ord-7145811c6cd946f5b9d7695fc4ca0cba
Source dataset
uspto-grants-2003_03
Patent number
US06534513B1

Reaction notes

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