Acetic Acid → HCID 67068492、化合物

HRID 536110ノート

反応式

HRID 536110 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH2:11])=[O:5])[CH3:2].[CH:13](=O)[CH:14]([CH3:16])[CH3:15].[BH3-]C#N.[Na+].CC(O)=O.[OH-].[Na+]>C(Cl)Cl.CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH:11][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:5])[CH3:2]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 6561Isobutyraldehyde2 回HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2 回HCID 67068498Ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate

生成物 1

HCID 67068492HCID 67068492、化合物収率 24%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

3-Amino-4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester (0.136 g, 0.58 mmol) and isobutyraldehyde (0.067 g, 0.93 mmol) were stirred in CH2Cl2/MeOH (1:1, 3 mL) at r.t. for 2 h. NaCNBH3 (0.065 g, 1.04 mmol) and HOAc (0.035 g, 0.58 mmol) were added and the mixture was stirred at r.t. for 2 h and then stirred at 50° C. for 16 h. Additional isobutyraldehyde (1 equiv.) and NaCNBH3 (0.5 equiv.) were added and the mixture was continued stirring at 50° C. overnight. The reaction mixture was neutralized with 2 M NaOH solution and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate), obtaining the title compound (0.040 g, 24%) as a white solid.

後処理

  1. stirringstirred at 50° C. for 16 h
  2. stirringthe mixture was continued stirring at 50° C. overnight
  3. customthe solvents were removed in vacuo
  4. extractionextracted with water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate)

出典と根拠

ORDレコード
ord-2d9b3c421cbe44938460dbd1e202c417
出典データセット
uspto-grants-2014_10
特許番号
US08859568B2

反応ノート

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