Piperidine → H-Val-Pro doxorubicin

HRID 882694Notes

Reaction equation

HRID 882694 reaction equation
N1CCCCC1.[NH:7](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:8]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10].[CH3:39][C@@H:40]1[O:45][C@@H:44]([O:46][C@@H:47]2[C:52]3=[C:53]([OH:70])[C:54]4[C:66](=[O:67])[C:65]5[C:60](=[CH:61][CH:62]=[CH:63][C:64]=5[O:68][CH3:69])[C:58](=[O:59])[C:55]=4[C:56]([OH:57])=[C:51]3[CH2:50][C@@:49]([OH:75])([C:71]([CH2:73][OH:74])=[O:72])[CH2:48]2)[CH2:43][C@H:42]([NH2:76])[C@@H:41]1[OH:77]>CN(C)C=O>[NH2:7][C@H:8]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10].[CH3:39][C@@H:40]1[O:45][C@@H:44]([O:46][C@@H:47]2[C:52]3=[C:53]([OH:70])[C:54]4[C:66](=[O:67])[C:65]5[C:60](=[CH:61][CH:62]=[CH:63][C:64]=5[O:68][CH3:69])[C:58](=[O:59])[C:55]=4[C:56]([OH:57])=[C:51]3[CH2:50][C@@:49]([OH:75])([C:71]([CH2:73][OH:74])=[O:72])[CH2:48]2)[CH2:43][C@H:42]([NH2:76])[C@@H:41]1[OH:77]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 131729870Fmoc-Val-Pro doxorubicin

Product 1

HCID 131729871H-Val-Pro doxorubicinYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of piperidine in dimethylformamide 50% (1.92 mL) was added to Fmoc-Val-Pro-doxorubicin (F) (29.7 mg, 0.03 mmol) and the reaction mixture was stirred at room temperature for 1 minute (the reaction colour changes form red to purple). Then, the reaction mixture was evaporated to dryness under reduced pressure and the residue thus obtained was purified by reverse phase chromatography with water/acetonitrile (70:1) to give the deprotected compound G (50% yield)

Workup

  1. customform red to purple)
  2. customThen, the reaction mixture was evaporated to dryness under reduced pressure
  3. customthe residue thus obtained
  4. customwas purified by reverse phase chromatography with water/acetonitrile (70:1)

Sources & evidence

ORD record
ord-0b684c819b1449a88100176c90eb6a4f
Source dataset
uspto-grants-2012_08
Patent number
US08236756B2

Reaction notes

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