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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium cyanoborohydride → (1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

HRID 1172223
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HRID 1172223 반응식
[C:1]1([C:7]2([NH:13][C:14](=[O:16])[CH3:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][C:18]1[CH:43]=[CH:42][C:21]([CH2:22][N:23]([CH3:41])[C:24]([C@@:26]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:28][C@H:27]2/[CH:29]=[CH:30]/[CH:31]=O)=[O:25])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>C(O)C>[F:17][C:18]1[CH:43]=[CH:42][C:21]([CH2:22][N:23]([CH3:41])[C:24]([C@@:26]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:28][C@H:27]2/[CH:29]=[CH:30]/[CH2:31][N:10]2[CH2:11][CH2:12][C:7]([NH:13][C:14](=[O:16])[CH3:15])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9]2)=[O:25])=[CH:20][CH:19]=1
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참가 물질

5

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HCID 5003444Sodium cyanoborohydrideHCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 86609590(1S,2S)-1-(3,4-Dichloro-phenyl)-2-((E)-3-oxo-propenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

생성물 1

HCID 67423469(1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

시약·촉매·용매 1

HCID 702
Ethanol
용매
2회

실험 절차

N-(4-Phenyl-piperidin-4-yl)-acetamide (140 mg, 0.64 mmol) dissolved in ethanol (3 ml) is added to (1S,2S)-1-(3,4-Dichloro-phenyl)-2-((E)-3-oxo-propenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide dissolved in ethanol (5 ml) followed by dropwise addition of sodium cyanoborohydride (1.0M in THF, 1.97 ml, 1.97 mmol) at 0° C. After complete addition the mixture is kept at ambient temperature for 2 hours. The reaction is quenched by addition of sodium bicarbonate (3 ml, sat.) and the ethanol is removed by means of evaporation. Ethyl acetate (30 ml) is added to the remanence. The organic fraction is washed successively with sodium bicarbonate (10 ml, sat.) and brine (10 ml, sat.), dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with ethyl acetate:ethanol:triethylamine (95:0:5)-(90:5:5) to furnish the title compound as an oil. Yield 81 mg (27%). LC/MS (m/z) 610.3 (M+H+).

후처리

  1. additionAfter complete addition the mixture
  2. customThe reaction is quenched by addition of sodium bicarbonate (3 ml, sat.)
  3. customthe ethanol is removed by means of evaporation
  4. additionEthyl acetate (30 ml) is added to the remanence
  5. washThe organic fraction is washed successively with sodium bicarbonate (10 ml, sat.) and brine (10 ml, sat.)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with ethyl acetate:ethanol:triethylamine (95:0:5)-(90:5:5)

출처 및 근거

ORD 기록
ord-b7c10c9369f745fb96e72181082299de
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834008B2

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