Sodium Hydroxide → HCID 68768194, compound

HRID 1173017Notes

Reaction equation

HRID 1173017 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=2)=[CH:11][C:10]=1[Cl:30])=[O:5])C.[OH-].[Na+]>CO>[Cl:30][C:10]1[CH:11]=[C:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=2)[CH:13]=[CH:14][C:9]=1[C@@H:7]1[CH2:8][C@H:6]1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 91308375HCID 91308375, compound

Product 1

HCID 68768194HCID 68768194, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of enantiomerically enriched-(trans)-ethyl-2-[2-chloro-4-({[3-(phenyloxy)phenyl]methyl}amino)phenyl]cyclopropanecarboxylate (III-2f) (0.269 g, 0.64 mmol) and 0.75 mL of 15% aqueous sodium hydroxide in 8 mL of methanol was heated at reflux for 1.5 hours. Methanol was evaporated and the residue was dissolved in water and acidified with concentrated hydrochloric acid. The resulting suspension was extracted with dichloromethane, the organic phase was washed with water and dried over anhydrous sodium sulfate and the solvent evaporated to give 0.217 g (86% yield) of the title compound as a white solid. NMR (400 MHz, CDCl3) δ 7.32 (t, J=7.33 Hz, 2H), 7.28 (t, J=7.69 Hz, 1H), 7.09 (t, J=6.41 Hz, 1H), 7.06 (d, J=7.87 Hz, 1H), 6.98 (d, J=7.51 Hz, 2H), 6.99 (m, 1H), 6.90 (dd, J=7.87 Hz, 1.65 Hz, 1H), 6.80 (d, J=8.42 Hz, 1H), 6.61 (d, J=2.56 Hz, 1H), 6.40 (dd, J=8.42 Hz, 2.38 Hz, 1H), 4.26 (s, 2H), 2.66 (m, 1H), 1.70 (m, 1H), 1.60 (m, 1H), 1.33 (m, 1H). ES-MS m/z 394 (MH)+. [α]25,D=+170° (chloroform, c=1.2). Product was determined to be 98% ee by chiral SFC according to Method 1.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customMethanol was evaporated
  3. dissolutionthe residue was dissolved in water
  4. extractionThe resulting suspension was extracted with dichloromethane
  5. washthe organic phase was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-c98c243a116e4377a6ee294a34d1487d
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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