Hydrochloric Acid → Fmoc-Val-Pro doxorubicin

HRID 882693

Reaction equation

HRID 882693 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 131729870Fmoc-Val-Pro doxorubicinYield 45%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-eb975f8915e54d90b81363eb67c62aed
Source dataset
uspto-grants-2012_08
Patent number
US08236756B2

Linked notes

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