Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 32847노트

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HRID 32847 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][CH3:19].O1CCCC1>S(Cl)(Cl)=O.CO>[CH3:17][N:18]([CH3:19])[C:14]([C:12]1[N:13]=[C:9]([NH2:8])[S:10][CH:11]=1)=[O:16].[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:18]([CH3:19])[CH3:17])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

생성물 2

HCID 545942972-amino-N,N-dimethyl-1,3-thiazole-4-carboxamideHCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester수율 48%

시약·촉매·용매 2

HCID 887Methanol용매HCID 24386Thionyl Chloride용매

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온도
80 °C

실험 절차

2-Amino-thiazole-4-carboxylic acid dimethylamide was prepared as follows. (1) A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (0.5 g, 2 mmol) (prepared as described in Examples 4a and 4b) in thionyl chloride (10 mL) was heated at reflux (80° C.) for 2 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added a 2 M solution of dimethylamine in tetrahydrofuran (10 mL, 20 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 20 hours and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a yellow foam (0.26 g, 48%).

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography over silica gel
  4. washeluted with 2:1 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-fee1464fa8e24b5288cdc61705cefdd9
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427635B2

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