Dimethylamine → Boc-Lys(Z)-Tyr(tBu)-Lys(Z)

HRID 592509노트

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HRID 592509 반응식
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:15]([NH:17][C@H:18]([C:34]([O:36]C)=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.CNC.[NH:58]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[C@H:59]([C:75]([OH:77])=O)[CH2:60][CH2:61][CH2:62][CH2:63][NH:64][C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.C(Cl)(Cl)Cl.CO>[NH:58]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[C@H:59]([C:75]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:34]([OH:36])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[CH:8][CH:9]=1)=[O:77])[CH2:60][CH2:61][CH2:62][CH2:63][NH:64][C:65]([O:67][CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:66]

참가 물질

9

반응물 5

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724765Boc-Lys(Z)-OHHCID 131734556Fmoc-Tyr(tBu)-Lys(Z)-OMe

생성물 1

HCID 131734557Boc-Lys(Z)-Tyr(tBu)-Lys(Z)수율 65%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Fmoc-Tyr(tBu)-Lys(Z)-OMe (7.72 g, 10.49 mmol) in THF (105 mL), was added dimethyl amine (52.5 mL, 2 M, 104.9 mmol). This reaction was allowed to reach room temperature and stirred for 1.5 h. At this time, the reaction mixture was concentrated in vacuo. To the yellowish solid, was added DCM (225 mL) and DMF (45 mL). To this solution, was added Boc-Lys(Z)—OH (4.19 g, 11.01 mmol), then HOBt (1.488 g, 11.01 mmol), then EDC.HCl (2.112 g, 11.01 mmol). This solution was allowed to stir for 8 h at which time the organic solution was washed with 1 N HCl (3×100 mL), then saturated NaHCO3 (3×100 mL), and finally H2O (3×100 mL). The organic layer became jelly like and MeOH was added to break the gel. The organic layer was dried over MgSO4 and concentrated in vacuo to yield a white solid. Column chromatography (0-1% MeOH, CHCl3) afforded the product (5.51 g, 65% yield).

후처리

  1. customto reach room temperature
  2. concentrationAt this time, the reaction mixture was concentrated in vacuo
  3. additionTo the yellowish solid, was added DCM (225 mL) and DMF (45 mL)
  4. stirringto stir for 8 h at which time the organic solution
  5. washwas washed with 1 N HCl (3×100 mL)
  6. additionwas added
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto yield a white solid

출처 및 근거

ORD 기록
ord-ae05d48773a94afc8ab9df5edd88a264
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238697B2

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