Methanamine, N-methoxy-, hydrochloride (1:1) → N,2-dimethoxy-N-methyl-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetamide

HRID 56555

반응식

HRID 56555 반응식
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)=[CH:9][CH:8]=1)[C:4]([OH:6])=O.C(N(CC)C(C)C)(C)C.COCCN(S(F)(F)F)CCOC.Cl.[CH3:42][NH:43][O:44][CH3:45].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:45][O:44][N:43]([CH3:42])[C:4](=[O:6])[CH:3]([O:2][CH3:1])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)=[CH:9][CH:8]=1

참가 물질

7

반응물 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 584319992-methoxy-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetic acid

생성물 1

HCID 58432087N,2-dimethoxy-N-methyl-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetamide수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-methoxy-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetic acid (0.87 g, 3.5 mmol) in anhydr CH2Cl2 (10 ml) was added N,N-diisopropylethylamine (1.36 g, 10.5 mmol) while cooling over an ice bath. bis(2-Methoxyethyl)aminosulfur trifluoride (0.93 g, 4.2 mmol) was added and stirred 15 min. N,O-Dimethylhydroxylamine HCl (0.512 g, 5.25 mmol) was added and the mixture was allowed to stir overnight while warming to room temp. Saturated aqueous NaHCO3 (15 ml) was added and stirred for 5 min. The organic layer was dried over Na2SO4 and evaporated to dryness. Purification by chromatography (60% EtOAc-hexanes) gave N,2-dimethoxy-N-methyl-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetamide as a clear oil (0.425 g, 42% yield).

후처리

  1. temperaturewhile cooling over an ice bath
  2. stirringto stir overnight
  3. stirringstirred for 5 min
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customPurification by chromatography (60% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-ffc7825c7ae34153b58a106308aed439
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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