Sodium Hydroxide → HCID 131720729, compound

HRID 964937Notes

Reaction equation

HRID 964937 reaction equation
C(O)(=O)C(O)=[O:3].[CH3:7][N:8]([CH2:10][C@H:11]1[O:32][N:14]2[C:15]3[CH:27]=[C:26]([C:28]([O:30]C)=[O:29])[CH:25]=[CH:24][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C@@H:13]2[CH2:12]1)[CH3:9].[OH-].[Na+]>C(O)C.O>[OH2:3].[CH3:9][N:8]([CH2:10][C@H:11]1[O:32][N:14]2[C:15]3[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C@@H:13]2[CH2:12]1)[CH3:7].[CH3:9][N:8]([CH2:10][C@H:11]1[O:32][N:14]2[C:15]3[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C@@H:13]2[CH2:12]1)[CH3:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131720731HCID 131720731, compound

Product 1

HCID 131720729HCID 131720729, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(±)-Methyl cis-2-[(dimethylamino)methyl]-3,3a-dihydro-2H-dibenz[b,f]isoxazolo-[2,3-d][1,4]oxazepine-11-carboxylate ethanedioate(1:1)(1.53g), prepared following the procedure in example 7, in ethanol (60 ml) was added dropwise to a mixture of sodium hydroxide (0.3 g) in water (7.5 ml) and the mixture was stirred and refluxed for 2 hours. The solvent was evaporated in vacuo and the residue was acidified with HCl (4N) to a pH of 3.6. The precipitate was filtered off, dried with P2O5 and purified by short pad column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 7/3). The pure fractions were collected and evaporated and the residue (1 g) was treated with CH2Cl2 /C2H5OH/H2O 25ml/5ml/5ml. The precipitate was filtered off and dried, yielding 0.5 g (38%) of (±)-cis-2-[(dimethylamino)methyl]-3,3a-dihydro-2H-dibenz[b,f]isoxazolo[2,3-d][1,4]oxazepine-11-carboxylic acid hemihydrate; mp. 229.8° C. (comp. 4).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was evaporated in vacuo
  3. filtrationThe precipitate was filtered off
  4. dry with materialdried with P2O5
  5. custompurified by short pad column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 7/3)
  6. customThe pure fractions were collected
  7. customevaporated
  8. additionthe residue (1 g) was treated with CH2Cl2 /C2H5OH/H2O 25ml/5ml/5ml
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-41ac23da587340b3921918277afdd7c5
Source dataset
uspto-grants-1998_06
Patent number
US05773433

Reaction notes

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