Triethylamine → (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate

HRID 449480

反応式

HRID 449480 の反応式
ClC(Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.[NH2:14][C:15](=O)[C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[C:15]([C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=1)#[N:14]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 20079Trichloroacetic anhydrideHCID 59496729(S)-tert-butyl 1-amino-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 59496725(S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trichloroacetic acid anhydride (120 mg, 0.39 mmol) was added slowly to a solution of (S)-tert-butyl 1-amino-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 0.2 mmol) in methylene chloride (3 mL) and triethylamine (86 uL, 0.62 mmol) at 0° C. The reaction was stirred for 1 h. at 0° C. The reaction was quenched with saturated NaHCO3 and was extracted with ethyl acetate. The organic phase was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain the (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate (40 mg, 80%) as clear oil. Analytical LCMS (M+Na)+: m/z=327.0.

後処理

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was washed with water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product, which
  8. customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

出典と根拠

ORDレコード
ord-ded7723687b84368be83e778da5e538d
出典データセット
uspto-grants-2013_07
特許番号
US08481732B2

関連ノート

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