Hydrochloric Acid → Fmoc-Val-Pro doxorubicin

HRID 882693

反応式

HRID 882693 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 131729870Fmoc-Val-Pro doxorubicin収率 45%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eb975f8915e54d90b81363eb67c62aed
出典データセット
uspto-grants-2012_08
特許番号
US08236756B2

関連ノート

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