Diisopropylethylamine → HCID 86714206, compound

HRID 1484210Notes

Reaction equation

HRID 1484210 reaction equation
[CH:1]1(O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[CH3:19][C@@H:20]1[O:25][C@@H:24]([O:26][C@@H:27]2[C:32]3=[C:33]([OH:50])[C:34]4[C:46](=[O:47])[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][C:44]=5[O:48][CH3:49])[C:38](=[O:39])[C:35]=4[C:36]([OH:37])=[C:31]3[CH2:30][C@@:29]([OH:55])([C:51]([CH2:53][OH:54])=[O:52])[CH2:28]2)[CH2:23][C@H:22]([NH2:56])[C@@H:21]1[OH:57].Cl>CN(C=O)C>[CH:1]1=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1.[CH3:19][C@@H:20]1[O:25][C@@H:24]([O:26][C@@H:27]2[C:32]3=[C:33]([OH:50])[C:34]4[C:46](=[O:47])[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][C:44]=5[O:48][CH3:49])[C:38](=[O:39])[C:35]=4[C:36]([OH:37])=[C:31]3[CH2:30][C@@:29]([OH:55])([C:51]([CH2:53][OH:54])=[O:52])[CH2:28]2)[CH2:23][C@H:22]([NH2:56])[C@@H:21]1[OH:57]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443939Doxorubicin HydrochlorideHCID 12599566HCID 12599566, compound

Product 1

HCID 86714206HCID 86714206, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar fashion, from the PNP-derivative 34 derived from the major alcohol 31 (22 mg, 0.0756 mmol) in 7.2 g DMF, after reaction with diisopropylethylamine (80 mg, 0.62 mmol) and doxorubicin hydrochloride (47.7 mg, 0.0822 mmol), followed by removal of the solvent under high vacuum, chromatography and TBME/heptane treatment major-38 was obtained (21 mg, 0.030 mmol, 30%). The filtrate contained an additional amount of product.

Workup

  1. customfollowed by removal of the solvent under high vacuum, chromatography and TBME/heptane treatment
  2. customwas obtained (21 mg, 0.030 mmol, 30%)

Sources & evidence

ORD record
ord-d25b0fa8f6fe46c3a183bfea42f53c40
Source dataset
uspto-grants-2016_08
Patent number
US09421274B2

Reaction notes

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