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

HRID 449469

反応式

HRID 449469 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07283d0ad71c4b188f3a959a375e84f6
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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