Trifluoroacetic acid → Nalpha,Ndelta-Bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-Naphthylamide

HRID 1067079ノート

反応式

HRID 1067079 の反応式
[C:1]([NH:8][C@@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[CH:59][C:58]=1[NH:67][C:68](=[O:86])[CH2:69][N:70](C(OC(C)(C)C)=O)[CH2:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[CH:59][C:58]=1[NH:67][C:68](=[O:86])[CH2:69][N:70]([C:21](=[O:23])[C@@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 81531Diisopropylethylamine2 回HCID 2733179PyBroPHCID 7015801HCID 7015801、化合物HCID 21195850Boc-N-(phenethyl)glycine 2-naphthylamide

生成物 1

HCID 20662194Nalpha,Ndelta-Bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-Naphthylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A solution (0° C.) of Nα,Nδ-bis-Boc-D-ornithine (130 mg, 0.39 mmol), diisopropylethylamine (1.6 mmol) and methylene chloride (10 mL) was treated with PyBroP (275 mg, 0.59 mmol) and kept at 0° C. for 30 min. In another reaction, a solution of Boc-N-(phenethyl)glycine 2-naphthylamide (240 mg, 0.59 mmol) (made by coupling of N-Boc-N-(phenethyl)glycine and 2-naphthylamine) and trifluoroacetic acid (3 mL) was stored at 24° C. for 1 hr and then concentrated in vacuo. The residue was coevaporated twice with methylene chloride and the resultant solid resuspended in methylene chloride (10 mL) and treated with diisopropylethylamine (1.2 mmol). The two solutions were mixed and stirred at 25° C. for 1 hr at which time the mixture was washed with 1M hydrochloric acid (2×25 mL), sat. sodium bicarbonate (25 mL), and brine (25 mL). The organic layer was dried over anhydrous sodium sulfate and adsorbed onto silica gel (500 mg) and applied to a column prepacked with silica gel. The column was eluted with ethyl acetate:hexane (50:50, v:v) to afford the titled compound.

後処理

  1. customIn another reaction
  2. concentrationconcentrated in vacuo
  3. additionThe two solutions were mixed
  4. washwas washed with 1M hydrochloric acid (2×25 mL), sat. sodium bicarbonate (25 mL), and brine (25 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. washThe column was eluted with ethyl acetate:hexane (50:50, v:v)

出典と根拠

ORDレコード
ord-20d1efb98bf347588c2e1eab785817b9
出典データセット
uspto-grants-2001_06
特許番号
US06245746B1

反応ノート

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