tert-butyl (R)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxymethyl]pyrrolidine-1-carboxylate → methyl 6-amino-3-bromo-2-((R)-1-pyrrolidin-2-ylmethoxy)benzoate

HRID 715946ノート

反応式

HRID 715946 の反応式
[Br:1][C:2]1[C:7]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)=[C:6]([C:22]([O:24][CH3:25])=[O:23])[C:5]([N:26](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:26][C:5]1[C:6]([C:22]([O:24][CH3:25])=[O:23])=[C:7]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[C:2]([Br:1])=[CH:3][CH:4]=1

参加物

4

反応物 1

HCID 71003908tert-butyl (R)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxymethyl]pyrrolidine-1-carboxylate2 回

生成物 1

HCID 86712110methyl 6-amino-3-bromo-2-((R)-1-pyrrolidin-2-ylmethoxy)benzoate収率 100.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of tert-butyl (R)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxymethyl]pyrrolidine-1-carboxylate (Intermediate 8, 3.15 g) in TFA (20 mL) and DCM (20 mL) was stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and washed with aqueous potassium carbonate solution. The aqueous layer was extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give methyl 6-amino-3-bromo-2-((R)-1-pyrrolidin-2-ylmethoxy)benzoate (1.65 g) as a colourless gum.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with aqueous potassium carbonate solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-602a60a6fd664b14b68823f63885bb2d
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

読み込み中…