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2-Phenylglycine → 2-(4-Chlorobutanamido)-2-phenylacetic acid

HRID 404664
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HRID 404664 반응식
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>O1CCOCC1.O>[Cl:12][CH2:13][CH2:14][CH2:15][C:16]([NH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:17]
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참가 물질

5

반응물 2

HCID 38662-PhenylglycineHCID 783704-Chlorobutyryl chloride

생성물 1

HCID 866889262-(4-Chlorobutanamido)-2-phenylacetic acid수율 38.9%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

2-Amino-2-phenylacetic acid (1.00 g, 6.62 mmol) and TEA (2.77 ml, 19.8 mmol) were dissolved in a mixture of dioxane (13.2 ml) and water (13.2 ml). The mixture was cooled at 0° C. with an ice-bath and 4-chlorobutanoyl chloride (814 μl, 7.28 mmol) was added dropwise. The mixture was stirred at the same temperature for 1 hour and then dioxane was evaporated. The aqueous solution was acidified with 1N HCl and then was extracted three times with EtOAc (20 ml×3). The organic phase was dried (Na2SO4) and evaporated. The crude pale yellow oil was purified by flash chromatography (DCM/MeOH=9/1) and the collected compound was triturated with Et2O (about 15 ml) to obtain the title compound (658 mg, 38.9% yield) as a white solid.

후처리

  1. customdioxane was evaporated
  2. extractionwas extracted three times with EtOAc (20 ml×3)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe crude pale yellow oil was purified by flash chromatography (DCM/MeOH=9/1)
  6. customthe collected compound was triturated with Et2O (about 15 ml)

출처 및 근거

ORD 기록
ord-27a511d631f44ac1a685c2fde43c258e
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748613B2

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