Acetic Acid → HCID 67068492, 화합물

HRID 536110노트

반응식

HRID 536110 반응식
[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]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 6561Isobutyraldehyde2회HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2회HCID 67068498Ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate

생성물 1

HCID 67068492HCID 67068492, 화합물수율 24%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d9b3c421cbe44938460dbd1e202c417
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859568B2

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