4-Methylmorpholine → Fmoc-Asp(Ot-Bu)-Trp-OBzl

HRID 637009

反応式

HRID 637009 の反応式
[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].C1CN([P+](ON2N=[N:55][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:49]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:81][C@H:82]([C:93]([O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)=[O:94])[CH2:83][C:84]1C2C(=CC=CC=2)N[CH:85]=1>C(Cl)Cl>[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11]([NH:81][C@H:82]([C:93]([O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)=[O:94])[CH2:83][C:84]1[C:49]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:55][CH:85]=1)=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:8])([CH3:7])[CH3:9]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2724635Fmoc-L-Asp(OtBu)-OHHCID 2724699PyBOPHCID 7016092L-Tryptophan benzyl ester

生成物 1

HCID 131722406Fmoc-Asp(Ot-Bu)-Trp-OBzl収率 77.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

41 mg of Fmoc-Asp(Ot-Bu)-OH was dissolved in 2 ml of methylene chloride, and the solution was cooled to 0° C. 78 mg of PyBOP, 20 mg of HOBt and 22 μl of NMM were added thereto in order and stirring was effected for 5 minutes, at 0° C. 2 ml of the methylene chloride solution containing 34 mg of H-Trp-OBzl (NO2) as obtained above was cooled to 0° C. and then added to the resulting reaction solution. Stirring was effected at 4° C. for 4 hours and at room temperature for 1 hour, the solvent was evaporated under reduced pressure, and the residue was purified with a silica gel column (manufactured by Merck Co., Kieselgel 60, 50 g, elution with chloroform:methanol=25:1), to obtain 53 mg of Fmoc-Asp(Ot-Bu)-Trp-OBzl (NO2). The obtained product was dissolved in 100 μl of DMF, 25 μl of piperidine was added. The mixture was then allowed to stand at room temperature for 10 minutes, and purified with a silica gel column (manufactured by Merck Co., Kieselgel 60, 50 g, elution with hexane:ethyl acetate=2:1), to obtain 1 mg of H-Asp(Ot-Bu)-Trp-OBzl (NO2).

後処理

  1. customas obtained
  2. temperatureabove was cooled to 0° C.
  3. additionadded to the resulting reaction solution
  4. stirringStirring
  5. waitwas effected at 4° C. for 4 hours and at room temperature for 1 hour
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified with a silica gel column (manufactured by Merck Co., Kieselgel 60, 50 g, elution with chloroform:methanol=25:1)

出典と根拠

ORDレコード
ord-a1b71068972c44c1aac4fac5267b2b84
出典データセット
uspto-grants-2001_02
特許番号
US06194195B1

関連ノート

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