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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Hydroxy-4-nitro-benzoic acid tert-butyl ester

HRID 714851
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HRID 714851 반응식
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N=C=N[CH2:19][CH2:20][CH2:21]N(C)C)C.ON1C2C=CC=C[C:29]=2N=N1.C(=O)([O-])O.[Na+]>C(O)(C)(C)C.C(N(CC)CC)C>[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:20]([CH3:21])([CH3:29])[CH3:19])=[O:5]
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참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692664-Nitrosalicylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium Bicarbonate

생성물 1

HCID 716010782-Hydroxy-4-nitro-benzoic acid tert-butyl ester수율 35.2%

시약·촉매·용매 2

HCID 6386
tert-Butanol
용매
HCID 8471Triethylamine용매

실험 절차

To a solution of 2-hydroxy-4-nitrobenzoic acid (5.0 g) in tert-butyl alcohol (100 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.4 g), 1-hydroxybenzotriazole (3.7 g) and triethylamine (7.6 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.3 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0dcf3759e4894e51a8bd95d0a14d02f9
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187453B2

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