Potassium Iodide → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-methyl-3-(1,3-thiazol-2-yl)-1,2-benzoxazole-5-carboxylic acid

HRID 577961Notes

Reaction equation

HRID 577961 reaction equation
C[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N:11]2[CH2:16][C@H:15]([CH3:17])[O:14][C@H:13]([CH3:18])[CH2:12]2)[C:5]([CH3:19])=[C:4](F)[C:3]=1[C:21](=[N:27][OH:28])[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:18][C@H:13]1[O:14][C@@H:15]([CH3:17])[CH2:16][N:11]([C:6]2[C:7]([C:8]([OH:10])=[O:9])=[CH:2][C:3]3[C:21]([C:22]4[S:23][CH:24]=[CH:25][N:26]=4)=[N:27][O:28][C:4]=3[C:5]=2[CH3:19])[CH2:12]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 136385151methyl 2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[(hydroxyimino)(1,3-thiazol-2-yl)methyl]-3-methylbenzoic acid2×

Product 1

HCID 673582146-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-methyl-3-(1,3-thiazol-2-yl)-1,2-benzoxazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[(hydroxyimino)(1,3-thiazol-2-yl)methyl]-3-methylbenzoic acid (Intermediate 195, 0.31 g, 0.8 mmol), K2CO3 (0.4 g, 2.3 mmol) and potassium iodide (0.03 g, 0.2 mmol) in DMF (10 mL) was heated at 130° C. for 12 hours. Solvents were removed under vacuum and the residue was treated with 1.5N hydrochloric acid and extracted with ethyl acetate, which was dried over sodium sulfate. Removal of solvent by vacuum afforded product. Yield: 0.18 g (62%).

Workup

  1. customSolvents were removed under vacuum
  2. additionthe residue was treated with 1.5N hydrochloric acid
  3. extractionextracted with ethyl acetate, which
  4. dry with materialwas dried over sodium sulfate
  5. customRemoval of solvent by vacuum
  6. customafforded product

Sources & evidence

ORD record
ord-3d409dd2d08346c1850f4baae389c38c
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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