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

HRID 487072

반응식

HRID 487072 반응식
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8]C(O)=CC=1.[CH3:21]I.[H-].[Na+].C(Cl)(Cl)Cl.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>CC(O)=O.CO>[C:14]([N:1]([CH3:21])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:30]=[CH:29][C:33]([O:32][CH3:31])=[CH:8][CH:9]=1)([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

참가 물질

8

반응물 5

HCID 6212ChloroformHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

생성물 1

HCID 7016369N-Boc-N-methyl-4-methoxy-L-phenylalanine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

To a solution of BOCTyr-OH (0.562 g, 2 mmol) in dry THF at 0° C. CH3I (2.8 g, 20 mmol) and NaH (0.24 g, 10 mmol) were added with vigorous stirring. The reaction mixture was stirred at r.t. for 24 hrs., then chilled, and NaH was destroyed by added EtOAc with water. The clear solution was evaporated to dryness and the residue was taken up in 10 ml of water. The aqueous solution was extracted with ether (2×10 ml), acidified with citric acid and extracted with EtOAc. The organic layer was washed with 5% hypo solution and water, dried over Na2SO4 and evaporated to dryness. The product was obtained as an oil: yield 0.56 g (91%); FABMS m/z 310 (M+H): 10. 0.5:0.5 Rf 51 (CHCl3 : MeOH: AcOH); Anal. Calcd. for C16H24NO4 : Mr 310.1663 (M+H); Found: Mr 310.1654 (M+H) (HRFABMS).

후처리

  1. customat 0° C
  2. temperature, then chilled
  3. customNaH was destroyed
  4. additionby added EtOAc with water
  5. customThe clear solution was evaporated to dryness
  6. extractionThe aqueous solution was extracted with ether (2×10 ml)
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with 5% hypo solution and water
  9. dry with materialdried over Na2SO4
  10. customevaporated to dryness
  11. customThe product was obtained as an oil

출처 및 근거

ORD 기록
ord-4ffcf12a5fe546309888e8f170d9446f
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294603

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