Hydrochloric Acid → Fmoc-Val-Pro doxorubicin

HRID 882693

반응식

HRID 882693 반응식
[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH3:33][C@@H:34]1[O:39][C@@H:38]([O:40][C@@H:41]2[C:46]3=[C:47]([OH:64])[C:48]4[C:60](=[O:61])[C:59]5[C:54](=[CH:55][CH:56]=[CH:57][C:58]=5[O:62][CH3:63])[C:52](=[O:53])[C:49]=4[C:50]([OH:51])=[C:45]3[CH2:44][C@@:43]([OH:69])([C:65]([CH2:67][OH:68])=[O:66])[CH2:42]2)[CH2:37][C@H:36]([NH2:70])[C@@H:35]1[OH:71].Cl.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH3:33][C@@H:34]1[O:39][C@@H:38]([O:40][C@@H:41]2[C:46]3=[C:47]([OH:64])[C:48]4[C:60](=[O:61])[C:59]5[C:54](=[CH:55][CH:56]=[CH:57][C:58]=5[O:62][CH3:63])[C:52](=[O:53])[C:49]=4[C:50]([OH:51])=[C:45]3[CH2:44][C@@:43]([OH:69])([C:65]([CH2:67][OH:68])=[O:66])[CH2:42]2)[CH2:37][C@H:36]([NH2:70])[C@@H:35]1[OH:71]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 31703DoxorubicinHCID 81531DiisopropylethylamineHCID 54198008Fmoc-Val-Pro-OH

생성물 1

HCID 131729870Fmoc-Val-Pro doxorubicin수율 45%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of Fmoc-Val-Pro-OH and doxorubicin. HCl (50 mg, 0.08 mmol) in DMSO (4 mL), was successively treated at room temperature with N-[(dimethylamino)1H-1,2,3-triazolo[4,5-b]pyridino-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) (36.0 mg, 0.09 mmol) and diisopropylethylamine (DIEA) (29.5 μL, 0.17 mmol). The reaction mixture was stirred at room temperature overnight. Then, the solvent was lyophilized and the residue was dissolved in ethyl acetate and washed with citric acid (10%), NaHCO3 (10%) and brine. The organic layer was dried (Na2SO4) and evaporated to dryness to give F (45% yield).

후처리

  1. washwashed with citric acid (10%), NaHCO3 (10%) and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated to dryness
  4. customto give F (45% yield)

출처 및 근거

ORD 기록
ord-eb975f8915e54d90b81363eb67c62aed
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236756B2

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