Isopropyl iodide → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate

HRID 449469

반응식

HRID 449469 반응식
[CH:1](I)([CH3:3])[CH3:2].[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:1]([CH3:3])[CH3:2])=[CH:21][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])=[O:11])([CH3:8])([CH3:6])[CH3:7]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 7019130Boc-Tyr-OMe

생성물 1

HCID 59496538(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate수율 90%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

Isopropyl iodide (30 uL, 0.3 mmol) was added to a mixture of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (50 mg, 0.2 mmol) (Aldrich, Cat. #469106) and potassium carbonate (35 mg, 0.25 mmol) in acetonitrile (2 mL). The reaction was heated at 60° C. overnight. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate (50 mg, 90%) as a white solid. Analytical LCMS (M+H-Boc)+: m/z=238.0.

후처리

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-07283d0ad71c4b188f3a959a375e84f6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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