Sodium Hydroxide → HCID 131728989, compound

HRID 2428204Notes

Reaction equation

HRID 2428204 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:6]1[CH2:7][CH2:8]2)=[O:4].[OH-].[Na+]>CCO>[C:35]([O:34][C:32]([N:31]1[C@H:9]2[CH2:8][CH2:7][C@@H:6]1[C@H:5]([C:3]([OH:4])=[O:2])[C@@H:11]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:23]([Cl:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=3[Cl:28])=[CH:16][CH:17]=1)[CH2:10]2)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728980HCID 131728980, compound

Product 1

HCID 131728989HCID 131728989, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a sol. of compound D2 (595 mg, 1.05 mmol) in EtOH (6.00 mL) was added aq. 1M NaOH (2.0 mL), and the resulting mixture was stirred at rt for 1 h, and at 70° C. overnight. The mixture was partially concentrated under reduced pressure, and the aq. residue was acidified with aq. 2M HCl. The mixture was extracted with EtOAc. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (573 mg, 98%) that was used further without purification. LC-MS: tR=1.11 min; ES+: 534.91.

Workup

  1. customat 70° C.
  2. customovernight
  3. concentrationThe mixture was partially concentrated under reduced pressure
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-29ad6abb688140b0afc0a9fb2628b45e
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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