Acetic Acid → HCID 86623432, compound

HRID 1664239Notes

Reaction equation

HRID 1664239 reaction equation
[OH:1][CH:2]1[CH:7]([NH:8][CH2:9][CH2:10][CH2:11][CH:12]2[N:16]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C@H:28]4[C@H:33]([O:34]C(=O)C)[C@@H:32]([O:38]C(=O)C)[C@H:31]([O:42]C(=O)C)[C@@H:30]([C:46]([O:48]C)=[O:47])[O:29]4)=[C:23]([NH:50][C:51](=[O:72])[CH2:52][CH2:53][NH:54]C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH:22]=3)=[O:18])[CH2:15][CH2:14][O:13]2)[CH2:6][CH:5]([O:73][CH:74]2[C:91]3[C:78](=[C:79]([OH:97])[C:80]4[C:81](=[O:96])[C:82]5[C:87]([C:88](=[O:93])[C:89]=4[C:90]=3[OH:92])=[C:86]([O:94][CH3:95])[CH:85]=[CH:84][CH:83]=5)[CH2:77][C@@:76]([OH:102])([C:98](=[O:101])[CH2:99][OH:100])[CH2:75]2)[O:4][CH:3]1[CH3:103].C(O)(=O)C.N1CCCCC1>CO.O.CN(C=O)C>[NH2:54][CH2:53][CH2:52][C:51]([NH:50][C:23]1[CH:22]=[C:21]([CH2:20][O:19][C:17]([N:16]2[CH2:15][CH2:14][O:13][CH:12]2[CH2:11][CH2:10][CH2:9][NH:8][CH:7]2[CH2:6][CH:5]([O:73][CH:74]3[C:91]4[C:78](=[C:79]([OH:97])[C:80]5[C:81](=[O:96])[C:82]6[C:87]([C:88](=[O:93])[C:89]=5[C:90]=4[OH:92])=[C:86]([O:94][CH3:95])[CH:85]=[CH:84][CH:83]=6)[CH2:77][C@@:76]([OH:102])([C:98](=[O:101])[CH2:99][OH:100])[CH2:75]3)[O:4][CH:3]([CH3:103])[CH:2]2[OH:1])=[O:18])[CH:26]=[CH:25][C:24]=1[O:27][C@@H:28]1[O:29][C@H:30]([C:46]([OH:48])=[O:47])[C@@H:31]([OH:42])[C@H:32]([OH:38])[C@H:33]1[OH:34])=[O:72]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 86623431HCID 86623431, compound

Product 1

HCID 86623432HCID 86623432, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of the doxorubicin oxazolidine 16 (30 mg, 0.021 mmol) in methanol (4 mL) was added a solution of LiOH monohydrate (8.8 mg, 0.21 mmol) in water (2 mL). The mixture was stirred for 35 min and was neutralized with acetic acid (8 uL, 0.21 mmol) to a pH of approximately 7. The mixture was concentrated under reduced pressure to give a residue which was dissolved in DMF (4 mL) and treated with piperidine (1 mL). The reaction mixture was stirred for 5 min, before being concentrated under reduced pressure. The residue was purified via preparative HPLC to yield 6.1 mg (27%) of product: LC-MS m/z (ES+), 1069.13 (M+H)+, 5.64 min.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue which
  3. stirringThe reaction mixture was stirred for 5 min
  4. concentrationbefore being concentrated under reduced pressure
  5. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-f746d5228459447b9b47d7386fa30546
Source dataset
uspto-grants-2011_10
Patent number
US08039273B2

Reaction notes

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