p-Toluenesulfonic acid monohydrate → N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 1698930

反応式

HRID 1698930 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.O.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C:10]([O:12][CH3:25])=[O:11])=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 712438N-benzyloxycarbonyl-l-tyrosine

生成物 1

HCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester収率 96.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 15.6 g (49 mmol) (2S)-3-(4-hydroxyphenyl)-2-[(phenylmethoxy)carbonylamino]propanoic acid in 120 mL methanol was added 9.4 g (49 mmol) of p-toluenesulfonic acid monohydrate. The solution was heated to 70 ° C. for 2 h. After solution was cooled to room temperature, the methanol was removed under reduced pressure. The solid obtained was redissolved in 120 mL methylene chloride. The organic solution was then washed with dilute NaHCO3 solution twice and brine. The organic layer was dried with anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The crude mixture was chromatographed on a silica gel column using 40% ethyl acetate in hexanes as the eluent to yield 15.6 g (96%) of white solid as product: 1H NMR (300 MHz, CDCl3) δ7.38-7.30 (m, 5H), 6.93 (d, J=8.41 Hz, 2H), 6.81 (d, J=8.41 Hz, 2H), 5.39 (br s, 1H), 5.24 (d, J=9.29 Hz, 1H), 5.11 (d, J=12.32 Hz, 1H), 5.06 (d, J=12.29 Hz, 1H), 4.61 (m, 1H), 3.71 (s, 3H), 3.06 (dd, J=5.88, 14.06 Hz, 1H), 2.98 (dd, J=5.88, 14.06 Hz, 1H)

後処理

  1. temperatureAfter solution was cooled to room temperature
  2. customthe methanol was removed under reduced pressure
  3. customThe solid obtained
  4. washThe organic solution was then washed with dilute NaHCO3 solution twice
  5. dry with materialThe organic layer was dried with anhydrous MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe crude mixture was chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-708ded514bd64b18b1a7d9b4fbd38ad3
出典データセット
uspto-grants-2002_02
特許番号
US06344484B1

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