Sodium Hydroxide → (rac.)-(1R*,5S*)-7-{6-[2-(2,6-Dichloro-4-methyl-phenoxy)ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester

HRID 2428198Notes

Reaction equation

HRID 2428198 reaction equation
[Cl:1][C:2]([Cl:50])([Cl:49])[C:3]([O:6][C:7]([N:9]1[C@H:14]2[C:15]([C:37]([O:39]CC)=[O:38])=[C:16]([C:18]3[CH:19]=[N:20][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]4[C:33]([Cl:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[Cl:36])=[CH:22][CH:23]=3)[CH2:17][C@@H:10]1[CH2:11][N:12]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:13]2)=[O:8])([CH3:5])[CH3:4].[OH-].[Na+]>CCO>[Cl:50][C:2]([Cl:1])([Cl:49])[C:3]([O:6][C:7]([N:9]1[C@H:14]2[C:15]([C:37]([OH:39])=[O:38])=[C:16]([C:18]3[CH:19]=[N:20][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]4[C:33]([Cl:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[Cl:36])=[CH:22][CH:23]=3)[CH2:17][C@@H:10]1[CH2:11][N:12]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:13]2)=[O:8])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728973(rac.)-(1R*,5S*)-7-{6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic Acid 3-tert-butyl Ester 6-ethyl Ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) Ester

Product 1

HCID 131728985(rac.)-(1R*,5S*)-7-{6-[2-(2,6-Dichloro-4-methyl-phenoxy)ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound C5 (1.02 g, 1.3 mmol) was dissolved in EtOH (14 mL), and aq. 1M NaOH (6 mL) was added. The mixture was heated to 80° C., and stirred at this temperature for 3 h. The mixture was allowed to cool to rt, and the solvents were partially removed under reduced pressure. The residue was mixed with EtOAc, and this mixture was acidified with aq. 1M HCl. The phases were partitioned, and the aq. layer was extracted with EtOAc (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the crude title compound mixed with (rac.)-(1R*,5S*)-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-7-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester (864 mg, 87%), which was used further without purification. LC-MS: tR=1.15 min; ES+: 768.23.

Workup

  1. temperatureto cool to rt
  2. customthe solvents were partially removed under reduced pressure
  3. additionThe residue was mixed with EtOAc
  4. customThe phases were partitioned
  5. extractionthe aq. layer was extracted with EtOAc (2×)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customDrying under high vacuum

Sources & evidence

ORD record
ord-7ceeaffaed044506bb963e22b9c2f644
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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