Dimethylformamide → BOC-L-Met-L-Leu-OMe

HRID 354730

반응식

HRID 354730 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][S:5][CH3:6].CN(C)C=O.[NH2:22][C@H:23]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(N(CC)CC)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:22][C@H:23]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:9])[CH2:3][CH2:4][S:5][CH3:6]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 65105(+)-L-Leucine methyl ester2회HCID 89857Boc-L-methionine2회HCID 199401P,P-Diphenylphosphinic azide

생성물 1

HCID 13145580BOC-L-Met-L-Leu-OMe

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

6.225 g. (25 mole) of BOC-L-Met was dissolved in 160 ml. of degassed dimethylformamide and cooled under nitrogen to 0° C. 4.55 g. (25 mmole) of L-Leu-OMe was dissolved in 80 ml. of dimethylformamide and set aside. To the BOC-L-Met was added 5.38 ml. of diphenylphosphorylazide in 10% excess followed by 3.48 ml. of triethylamine in 10% excess, followed by the L-Leu-OMe. The reaction mixture was stirred at 0° C. for 3 hrs., then at room temperature for 16 hrs. The solution was concentrated and treated with 3:1 dimethylformamide/water and mixed bed resin, whereupon it crystallized out on the resin. The resin and crystals were filtered and the resin washed with dimethylformamide to isolate the product. The filtrate was then concentrated and recrystallized from ethyl acetate/hexane. 7.74 g. of product was obtained.

후처리

  1. wait, then at room temperature for 16 hrs
  2. concentrationThe solution was concentrated
  3. additiontreated with 3:1 dimethylformamide/water
  4. additionmixed bed resin
  5. customwhereupon it crystallized out on the resin
  6. filtrationThe resin and crystals were filtered
  7. washthe resin washed with dimethylformamide
  8. customto isolate the product
  9. concentrationThe filtrate was then concentrated
  10. customrecrystallized from ethyl acetate/hexane
  11. customof product was obtained

출처 및 근거

ORD 기록
ord-e822de6bebed4095a9a2165aa1c7d0a9
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377515

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