4-Methylmorpholine → Boc-Leu-Gln-Arg(Tos)-Leu-OH

HRID 647393ノート

反応式

HRID 647393 の反応式
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:29]([NH:31][C@H:32]([C:37]([OH:39])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:28])[NH:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[NH:50]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[C@H:51]([C:56]([O:58]N1C(=O)CCC1=O)=O)[CH2:52][CH:53]([CH3:55])[CH3:54].CN1CCOCC1.NCCN1CCNCC1>CN1CCCC1=O.[Pd].CO>[NH:50]([C:66]([O:68][C:69]([CH3:70])([CH3:71])[CH3:72])=[O:67])[C@H:51]([C:56]([NH:1][C@H:2]([C:8]([NH:10][C@H:11]([C:29]([NH:31][C@H:32]([C:37]([OH:39])=[O:38])[CH2:33][CH:34]([CH3:35])[CH3:36])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:28])[NH:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:58])[CH2:52][CH:53]([CH3:54])[CH3:55]

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 8795AminoethylpiperazineHCID 11023929Boc-Leu-OSuHCID 178427537HCID 178427537、化合物

生成物 1

HCID 178427533Boc-Leu-Gln-Arg(Tos)-Leu-OH収率 83%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

In 235 ml of N-methylpyrrolidone are dissolved 16.9 g (24 millimoles) of Z-Gln-Arg(Tos)-Leu-OH obtained according to the process of Example 1 and 8.7 g (26.4 millimoles) of Boc-Leu-OSu, and 2.64 ml of N-methylmorpholine is added to the solution. Then, 3 g of 10% Pd-C is added to the mixture, and the mixture is stirred for 5 hours in a current of H2. Then, N-(2-aminoethyl) piperazine is added to the mixture, the mixture is stirred for 1 hour and 100 ml of methanol is added to the mixture. The 10% Pd-C is recoved by filtration, and the mixture is concentrated under reduced pressure to distill N-methylpyrrolidone. The residue is added to a liquid mixture of 100 ml of ethyl acetate and 200 ml of a dilute aqueous solution of citric acid. The mixture is sufficiently stirred, and the ethyl acetate layer is recovered, washed with water, dried and concentrated under reduced pressure. Ether is added to the concentrate and the precipitate is recovered by filtration to obtain 15.6 g of intended Boc-Leu-Gln-Arg(Tos)-Leu-OH (the yield being 83.2%).

後処理

  1. customobtained
  2. additionis added to the solution
  3. stirringthe mixture is stirred for 1 hour
  4. filtrationThe 10% Pd-C is recoved by filtration
  5. concentrationthe mixture is concentrated under reduced pressure
  6. distillationto distill N-methylpyrrolidone
  7. additionThe residue is added to a liquid mixture of 100 ml of ethyl acetate and 200 ml of a dilute aqueous solution of citric acid
  8. stirringThe mixture is sufficiently stirred
  9. customthe ethyl acetate layer is recovered
  10. washwashed with water
  11. customdried
  12. concentrationconcentrated under reduced pressure
  13. additionEther is added to the
  14. concentrationconcentrate
  15. filtrationthe precipitate is recovered by filtration

出典と根拠

ORDレコード
ord-7d4697dbb33f44bb9df5956ccf7a0bd3
出典データセット
uspto-grants-1983_10
特許番号
US04407745

反応ノート

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