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

HRID 449480

반응식

HRID 449480 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ded7723687b84368be83e778da5e538d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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