Dicyclohexylcarbodiimide → benzyl [(R)-2-(1-allyl-1H-imidazol-4-yl)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

HRID 626637ノート

反応式

HRID 626637 の反応式
[CH2:1]([N:4]1[CH:8]=[C:7]([CH2:9][C@@H:10]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C:11]([OH:13])=O)[N:6]=[CH:5]1)[CH:2]=[CH2:3].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:50]([O:53][CH2:54][C@@H:55]([NH2:59])[CH:56]([CH3:58])[CH3:57])[CH:51]=[CH2:52]>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@@H:10]([C:11](=[O:13])[NH:59][C@H:55]([CH2:54][O:53][CH2:50][CH:51]=[CH2:52])[CH:56]([CH3:58])[CH3:57])[CH2:9][C:7]1[N:6]=[CH:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 58360494(S)-1-Allyloxymethyl-2-methylpropylamineHCID 67029144(R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

生成物 1

HCID 86655969benzyl [(R)-2-(1-allyl-1H-imidazol-4-yl)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of the material from step A in 180 ml of DMF was mixed with 4.18 g (27.32 mmol) of N-hydroxybenzotriazole and 5.64 g (27.32 mmol) of N,N′-dicyclohexylcarbodiimide and stirred at RT for 2 h. Addition of 3.56 g (24.84 mmol) of (S)-1-allyloxymethyl-2-methylpropylamine (1-1B) was followed by stirring at RT for a further 24 h and then concentration, and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC. After washing with saturated NaHCO3 solution, 5.02 g of the title compound are obtained.

後処理

  1. stirringby stirring at RT for a further 24 h
  2. concentrationconcentration
  3. customthe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. washAfter washing with saturated NaHCO3 solution, 5.02 g of the title compound
  9. customare obtained

出典と根拠

ORDレコード
ord-e19383f93e8c4519b4c70adcc4a56811
出典データセット
uspto-grants-2016_04
特許番号
US09309207B2

反応ノート

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