Potassium Carbonate → (S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

HRID 58364

反応式

HRID 58364 の反応式
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH:31]=[CH2:32]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:32][CH2:31][CH:30]=[CH2:29])=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 7019130Boc-Tyr-OMe

生成物 1

HCID 66846982(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

N-BOC-tyrosine methyl ester (10.0 g, 33.9 mmol) was dissolved in DMF (40 mL) and potassium carbonate (5.62 g, 40.7 mmol) and 4-bromo-1-butene (4.13 mL, 40.7 mmol) were added. The mixture was stirred at rt for 18 h before being diluted with EtOAc (120 mL) and partitioned with 1M hydrochloric acid. The organic phase was washed with hydrochloric acid and then with brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 3.20 g, 27%. Rf=0.82 (1/2 EtOAc/(50/70) petroleum ether).

後処理

  1. custompartitioned with 1M hydrochloric acid
  2. washThe organic phase was washed with hydrochloric acid
  3. dry with materialwith brine before being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  7. customto yield a white solid, 3.20 g, 27%

出典と根拠

ORDレコード
ord-53224240deee4475a371d6a18ca920cc
出典データセット
uspto-grants-2016_09
特許番号
US09434762B2

関連ノート

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