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Triethylamine → 6-methoxy-3-phenyl-1-propionylamino-1H-indene-2-carboxylic acid ethyl ester

HRID 19560
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HRID 19560 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[C:24](Cl)(=[O:27])[CH2:25][CH3:26].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62324Propionyl chloride2회HCID 116739651-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

생성물 1

HCID 115088626-methoxy-3-phenyl-1-propionylamino-1H-indene-2-carboxylic acid ethyl ester수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (50 mg, 0.16 mmol) prepared in Example 20 was dissolved in dichloromethane (10 mL), and propionyl chloride (150.38 mg, 0.14 mL, 1.62 mmol) and triethylamine (180.12 mg, 0.25 mL, 1.78 mmol) were added thereto in order at 0° C. The mixture was stirred for 24 hrs at RT, and an excess amount of propionyl chloride (2 mL) was further added thereto to be stirred for 15 hrs. The resulting mixture was washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 29 mg of the titled compound (yield: 50%).

후처리

  1. customat 0° C
  2. stirringto be stirred for 15 hrs
  3. washThe resulting mixture was washed with saturated saline
  4. extractionextracted with dichloromethane
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-e3b1b261e3074333bea20c1dd6c7cfe8
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745439B2

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