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Diisopropylamine → Ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-tert-butoxy-3-oxopentanoate

HRID 1967254
ノート
印刷プレビュー

反応式

HRID 1967254 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([OH:21])=O)[CH2:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(NC(C)C)(C)C.[C:41]([O:44][CH2:45][CH3:46])(=[O:43])[CH3:42]>C1COCC1.O.C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:13][O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:21])[CH2:42][C:41]([O:44][CH2:45][CH3:46])=[O:43])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 1715617Z-Ser(tBu)-OH

生成物 1

HCID 67105592Ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-tert-butoxy-3-oxopentanoate収率 62%

試薬・触媒・溶媒 3

HCID 176
Acetic Acid
溶媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of N-[(benzyloxy)carbonyl]-O-(tert-butyl)-L-serine (25.0 g) in dry THF (100 mL) was added 1,1′-carbonylbis-1H-imidazole (16.5 g) at 0° C. by small portions, and the mixture was stirred at room temperature overnight (solution 1). To a solution of diisopropylamine (25.7 g) in dry THF (330 mL) was added dropwise a 1.6 mol/L n-butyllithium-hexane solution (158.7 mL) under an argon atmosphere at −78° C. The mixture was stirred at −78° C. for 30 min, and a solution of ethyl acetate (24.8 mL) in dry THF (100 mL) was added dropwise. After the completion of the dropwise addition, the mixture was stirred for 30 min, and solution 1 was added dropwise. The mixture was stirred at −78° C. for 1 hr, and acetic acid (25 mL) was added to the reaction mixture. After warming to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=50:1→1:1) to give the title compound as a colorless oil (yield: 19.2 g, 62%).

後処理

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred for 30 min
  3. stirringThe mixture was stirred at −78° C. for 1 hr
  4. temperatureAfter warming to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=50:1→1:1)

出典と根拠

ORDレコード
ord-b582a89633bc47fdb438709f0f3c0936
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08420694B2

反応ノート

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