Tetrahydrofuran → (+/-)-tert-Butyl 1-(3-{[cyclopentyl(4-vinylphenyl)acetyl]amino}benzyl)cyclopropanecarboxylate

HRID 1475656노트

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HRID 1475656 반응식
[H-].[Na+].[CH:3]1([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:37]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]1([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=[CH2:37])=[CH:31][CH:30]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86667523(+/-)-Tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate

생성물 1

HCID 68170305(+/-)-tert-Butyl 1-(3-{[cyclopentyl(4-vinylphenyl)acetyl]amino}benzyl)cyclopropanecarboxylate

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

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온도
0 °C

실험 절차

39.0 mg (0.98 mmol, 60% in mineral oil) of sodium hydride were suspended in 3.0 ml of abs. THF, the mixture was cooled to 0° C. and 301.8 mg (0.84 mmol) of methyltriphenylphosphonium bromide were added. The mixture was stirred at 0° C. for 30 min, and 300 mg (0.65 mmol) of (+/−)-tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]amino}benzyl)cyclopropanecarboxylate were then added. The reaction mixture was stirred at RT overnight and then concentrated under reduced pressure. The residue was taken up in acetonitrile and filtered, and the filtrate obtained was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 219.3 mg (73.4% of theory) of the target compound.

후처리

  1. stirringThe reaction mixture was stirred at RT overnight
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered
  4. customthe filtrate obtained
  5. customwas purified by preparative RP-HPLC (mobile phase acetonitrile/water)

출처 및 근거

ORD 기록
ord-38c69bb09cc1405bad17f99eaad2dd80
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018258B2

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