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

HRID 354730

反応式

HRID 354730 の反応式
[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]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 65105(+)-L-Leucine methyl ester2 回HCID 89857Boc-L-methionine2 回HCID 199401P,P-Diphenylphosphinic azide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e822de6bebed4095a9a2165aa1c7d0a9
出典データセット
uspto-grants-1983_03
特許番号
US04377515

関連ノート

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