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

HRID 1475656ノート

反応式

HRID 1475656 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-38c69bb09cc1405bad17f99eaad2dd80
出典データセット
uspto-grants-2015_04
特許番号
US09018258B2

反応ノート

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