Glycine → N-(p-nitrobenzyloxycarbonyl)glycine

HRID 54804노트

반응식

HRID 54804 반응식
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C(O)C.O.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21](=O)[O:22]C2C=CC([N+]([O-])=O)=CC=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]>C(N(CC)CC)C>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][O:20][C:21]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:22])=[CH:17][CH:18]=1)([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 750GlycineHCID 19096565Water ethanolHCID 21829967Carbonic acid 4-Nitrophenyl (4-Nitrophenyl)methyl Ester

생성물 1

HCID 12187147N-(p-nitrobenzyloxycarbonyl)glycine수율 55.7%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

One and one half grams of glycine is slurried in 235 ml of a 80/20 minute of ethyl alcohol/water. To this is added 5.6 ml of triethylamine, solution occurs, followed by 6.36 g of product from Example 254. A precipitate forms and the reaction is stirred overnight at room temperature. The reaction mixture is concentrated in vacuo. The resulting oil is dissolved in water and ethyl alcohol, the pH is adjusted to 1.5 with concentrated hydrochloric acid and the volume is reduced. The reaction mixture is extracted with methylene chloride, the organic layer is washed with water and concentrated in vacuo. The residue is purified by chromatography (Silica gel: ethyl acetate) to give 2.83 g of the desired product.

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe resulting oil is dissolved in water
  3. extractionThe reaction mixture is extracted with methylene chloride
  4. washthe organic layer is washed with water
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography (Silica gel: ethyl acetate)

출처 및 근거

ORD 기록
ord-3ec5894e745847e89febf951cf65c25f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623081

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