L-Tartaric acid → HCID 11853487, compound

HRID 1805806Notes

Reaction equation

HRID 1805806 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:11]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH2:28][CH3:29])=[C:22]([O:25][CH3:26])[CH:23]=3)[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][C@@H:16]([OH:30])[CH2:17]3)[N:12]=2)=[CH:5][N:4]=1.[C:32]([OH:41])(=[O:40])[C@@H:33]([C@H:35]([C:37]([OH:39])=[O:38])[OH:36])[OH:34]>CC(C)=O.C(O)(C)C>[C:37]([C@@H:35]([C@H:33]([C:32]([OH:41])=[O:40])[OH:34])[OH:36])([OH:39])=[O:38].[CH3:31][N:2]([CH3:1])[C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:11]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH2:28][CH3:29])=[C:22]([O:25][CH3:26])[CH:23]=3)[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][C@@H:16]([OH:30])[CH2:17]3)[N:12]=2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 11853488(2R,4aR,10bR)-6-(2-Dimethylamino-4-methoxy-pyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-ol

Product 1

HCID 11853487HCID 11853487, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3776IsopropanolSolvent

Procedure

(2R,4aR,10bR)-6-(2-Dimethylamino-4-methoxy-pyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-ol (42.7 mg, 0.1 mmol) are dissolved in 0.5 ml of acetone. 16.5 mg (0.11 mmol) of L-tartaric acid (dissolved in 0.5 ml of a 75:15 mixture of acetone and isopropanol) are added. The crystals are filtered off and dried to obtain 42.9 mg (74%) of the title compound (m. p.: 249° C.).

Workup

  1. additionare added
  2. filtrationThe crystals are filtered off
  3. customdried

Sources & evidence

ORD record
ord-fd8e0d2fd3f64c728e7536af71827064
Source dataset
uspto-grants-2013_01
Patent number
US08354535B2

Reaction notes

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