Trifluoroacetic acid → methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate

HRID 595113ノート

反応式

HRID 595113 の反応式
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[C:13]([C:29]([O:31][CH3:32])=[O:30])[C:12]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:33][C:12]1[C:13]([C:29]([O:31][CH3:32])=[O:30])=[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][NH:18]2)[C:9]([Br:8])=[CH:10][CH:11]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86712822Tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate2 回

生成物 1

HCID 86712821methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate収率 88.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TFA (5 mL) was slowly added to a suspension of tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate (Intermediate 19, 3.55 g) in DCM (5 mL). The resultant dark solution was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution. The layers were separated and the aqueous layer was extracted with more ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate (1.64 g) as a dark oil.

後処理

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fd2e6b58ce0f43baa74117bcaa278b47
出典データセット
uspto-grants-2016_01
特許番号
US09242997B2

反応ノート

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