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

HRID 2428203Notes

Reaction equation

HRID 2428203 reaction equation
[Cl:1][C:2]([Cl:46])([Cl:45])[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])[CH3:43])[CH2:13]2)=[O:8])([CH3:5])[CH3:4].[OH-].[Na+]>CCO>[Cl:46][C:2]([Cl:1])([Cl:45])[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:29]([Cl:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=4[Cl:34])=[CH:22][CH:23]=3)[CH2:17][C@@H:10]1[CH2:11][N:12]([C:42](=[O:44])[CH3:43])[CH2:13]2)=[O:8])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728974(rac.)-(1R*,5S*)-3-Acetyl-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-6,9-dicarboxylic Acid 6-ethyl Ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) Ester

Product 1

HCID 131728988(rac.)-(1R*,5S*)-3-Acetyl-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-6,9-dicarboxylic acid 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a sol. of compound C9 (3.03 g, 3.81 mmol) in EtOH (30 mL) was added aq. 1M NaOH (15 mL). This mixture was heated to 80° C., and stirred at this temperature for 2.5 h. The mixture was partially concentrated under reduced pressure. The residue was acidified with aq. 2M HCl, and 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 mixed with (rac.)-(1R*,5S*)-3-acetyl-7-{6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-pyridin-3-yl}-3,9-diaza-bicyclo[3.3.1]non-7-ene-6,9-dicarboxylic acid 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester (2.70 g, quantitative yield) that was used further without purification. LC-MS: tR=1.08 min; ES+: 710.09.

Workup

  1. concentrationThe mixture was partially concentrated under reduced pressure
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-e47775dc3c474a2bb5333bb74d5724b7
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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