Water → N-Boc-N-methyl-4-methoxy-L-phenylalanine

HRID 1720092

反応式

HRID 1720092 の反応式
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15]C(O)=CC=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CI.[CH3:23]C(=O)OCC.O.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[C:1]([N:8]([CH3:23])[C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:31]=[CH:30][C:34]([O:33][CH3:32])=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

6

反応物 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

生成物 1

HCID 7016369N-Boc-N-methyl-4-methoxy-L-phenylalanine収率 95%

反応条件

温度
0 °C

実験手順

6.0 g of NaH suspension were washed by decantation 3 times with PE, 50 ml of THF were poured on, and the mixture was cooled to 0° C. Then 32 mmol of BOC-L-tyrosine dissolved in 110 ml of THF were slowly added dropwise, and subsequently 16 ml of methyl iodide were added. The suspension was stirred at RT with exclusion of light for 25 h, 50 ml of EA were added, and the mixture was cautiously hydrolyzed with water. It was concentrated under reduced pressure to a small volume, EA was added, and the mixture was acidified with 2N KHSO4. After extraction with EA, the organic phases were washed with 10% strength sodium thiosulfate solution, dried (MgSO4) and evaporated under reduced pressure. Yield: 95%.

後処理

  1. wash6.0 g of NaH suspension were washed by decantation 3 times with PE, 50 ml of THF
  2. additionwere poured on, and the mixture
  3. additionwere slowly added dropwise
  4. concentrationIt was concentrated under reduced pressure to a small volume, EA
  5. additionwas added
  6. extractionAfter extraction with EA
  7. washthe organic phases were washed with 10% strength sodium thiosulfate solution
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-c86972516fab465e8b0ba5ccbb34a320
出典データセット
uspto-grants-1996_04
特許番号
US05504189

関連ノート

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