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Sodium Iodide → (4-{Tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenoxy)-acetic acid methyl ester

HRID 1393109
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HRID 1393109 반응식
[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][C:7]=1[CH3:20].[I-].[Na+].Cl[CH2:25][C:26]1[S:30][C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)=[N:28][C:27]=1[CH3:41].[H-].[Na+].OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:25][C:26]2[S:30][C:29]([C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:36]=3)=[N:28][C:27]=2[CH3:41])=[CH:8][C:7]=1[CH3:20]
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7

반응물 5

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 67072259HCID 67072259, 화합물

생성물 1

HCID 69218315
(4-{Tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenoxy)-acetic acid methyl ester
수율 114.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid methyl ester (1.00 g, 3.39 mmol, example 17.3), sodium iodide (0.51 g, 3.39 mmol) and 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (1.09 g, 3.72 mmol, WO02/28433) in DMF (10 ml) was added within 10 min NaH (0.19 g, 55% in oil, 4.40 mmol). The reaction was stirred at 0° C. for 2 h, 30 min at RT and then neutralized with chilled aqueous 10% KHSO4 and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 2.14 g of (4-{tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenoxy)-acetic acid methyl ester, MS: 551.3 (MH+).

후처리

  1. extractionextracted with aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-b840ddfc68a849bea2396e3403c10e3f
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345067B2

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