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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 245501
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HRID 245501 반응식
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
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참가 물질

5

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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 acid2회

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7d025a70d40e48148a8165333a10d8dd
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658641B2

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