Potassium Hydroxide → HCID 54161940, compound

HRID 5841Notes

Reaction equation

HRID 5841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[N:10](C(=O)[C@@H]3CCCN3S(C3C=CC5C(=CC=CC=5)C=3)(=O)=O)[CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[NH:10][CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54292589(R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine

Product 1

HCID 54161940HCID 54161940, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (11.50 g, 0.019 mole), 86 % potassium hydroxide (15.0 g, 0.227 mole) and ethanol-water (10:1, 230 ml) is refluxed under argon for one hour. The reaction mixture is poured into ice water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water and saline, dried over sodium sulfate and distilled to remove the solvent. The residue is purified by silica gel column chromatography (CHCl3) and thereafter recrystallized from ethyl acetate-hexane to give (R)-(+)-3-(4-chlorophenyl)- 2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (3.74 g, 63%). M.p. 205°-206° C.

Workup

  1. temperatureis refluxed under argon for one hour
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with water and saline
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (CHCl3)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b83e9eb589e24776b7e8c40b1d8b288f
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Reaction notes

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