L-Tartaric acid → HCID 67022384, compound

HRID 406949Notes

Reaction equation

HRID 406949 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH3:27])=[C:20]([O:23][CH3:24])[CH:21]=3)[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][C@@H:14]([OH:28])[CH2:15]3)[N:10]=2)=[CH:5][N:4]=1.[C:30]([OH:39])(=[O:38])[C@@H:31]([C@H:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32]>ClCCl.CC(C)=O.C(O)(C)C>[C:35]([C@@H:33]([C@H:31]([C:30]([OH:39])=[O:38])[OH:32])[OH:34])([OH:37])=[O:36].[CH3:29][N:2]([CH3:1])[C:3]1[N:4]=[CH:5][C:6]([C:9]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH3:27])=[C:20]([O:23][CH3:24])[CH:21]=3)[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][C@@H:14]([OH:28])[CH2:15]3)[N:10]=2)=[CH:7][N:8]=1

Participants

6

Reactant 2

HCID 444305L-Tartaric acidHCID 11853490HCID 11853490, compound

Product 1

HCID 67022384HCID 67022384, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2R,4aR,10bR)-6-(2-Dimethylamino-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 1.0 ml of dichloromethane. 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 33.3 mg (61%) of the title compound (m.p.: 206° C.).

Workup

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

Sources & evidence

ORD record
ord-749320f93bc84f8cbde7143ff48319a0
Source dataset
uspto-grants-2014_06
Patent number
US08754218B2

Reaction notes

Loading…