Sodium Hydroxide → HCID 131728984, compound

HRID 2428196Notes

Reaction equation

HRID 2428196 reaction equation
C[O:2][C:3]([C:5]1[C@@H:6]2[N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:9]([CH2:10][C:11]=1[C:12]1[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]=1)[CH2:8][CH2:7]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:5]([C:3]([OH:4])=[O:2])=[C: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 131728981HCID 131728981, compound

Product 1

HCID 131728984HCID 131728984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Compound C2 (3.82 g, 6.80 mmol) was dissolved in EtOH (100 mL). The sol. was heated to 70° C., and aq. 1M NaOH (80 mL, 80 mmol) was added. The mixture was stirred at 80° C. for 3 h, and allowed to cool to rt. The solvents were partially removed under reduced pressure, and the residue was poured into a separatory funnel filled with EtOAc. Aq. 1M HCl was added until the aq. phase was acidic, and the phases were shaken and separated. The aq. layer was extracted with EtOAc (2×), and 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 mixed with (rac.)-(1R*,5S*)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-8-aza-bicyclo[3.2.1]oct-3-ene-2,8-dicarboxylic acid 8-tert-butyl ester (3.45 g, 93%) that was used further without purification. LC-MS: tR=1.13 min; ES+: 548.25.

Workup

  1. temperatureto cool to rt
  2. customThe solvents were partially removed under reduced pressure
  3. additionthe residue was poured into a separatory funnel
  4. additionfilled with EtOAc
  5. additionAq. 1M HCl was added until the aq. phase
  6. stirringthe phases were shaken
  7. customseparated
  8. extractionThe aq. layer was extracted with EtOAc (2×)
  9. dry with materialextracts were dried over MgSO4
  10. filtrationfiltered
  11. customthe solvents were removed under reduced pressure
  12. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-c11633dd3963490fa7d9a3ed35c6fc00
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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