Triphenylphosphine → Ethyl (2R)-2-(4-{1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate

HRID 1072707노트

반응식

HRID 1072707 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.O[C@@H:24]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:16]2[CH:17]=[CH:18][C:19]([O:22][C@H:24]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9877619Ethyl phenyllactate, (-)-HCID 223874754-[1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl]phenol

생성물 1

HCID 86588891Ethyl (2R)-2-(4-{1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate수율 54%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 4-[1-[2-(4-bromophenyl)ethan-1-yl]-5-methyl-1H-pyrrol-2-yl]phenol (3.00 g, 8.42 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.96 g, 10.1 mmol) and triphenylphosphine (2.65 g, 10.1 mmol) in toluene (30 ml) was added diethyl azodicarboxylate (1.76 g, 10.1 mmol) and refluxed for 20 hours under heating. The insoluble matter was filtered out and the filtrate was diluted with ethyl acetate. The obtained solution was washed with water and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 2.40 g (yield: 54.0%)

후처리

  1. temperaturerefluxed for 20 hours
  2. temperatureunder heating
  3. filtrationThe insoluble matter was filtered out
  4. additionthe filtrate was diluted with ethyl acetate
  5. washThe obtained solution was washed with water
  6. dry with materialdried over magnesium sulfate anhydride
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  9. customto give the object compound as an oily substance

출처 및 근거

ORD 기록
ord-9dd854018f0b40f189b12455cbdd0f1c
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911468B2

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