Leurosine sulfate → methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

HRID 1701091Notes

Reaction equation

HRID 1701091 reaction equation
[CH3:1][CH2:2][C@@:3]12[O:22][C@@H:21]1[C@@H:19]1[CH2:20][N:5]([CH2:6][CH2:7][C:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[NH:15][C:16]=3[C@@:17]([C:56]([O:58][CH3:59])=[O:57])([C:23]3[CH:24]=[C:25]4[C@:33]56[C@@H:37]7[C@:38]([CH2:53][CH3:54])([C@@H:42]([O:49][C:50]([CH3:52])=[O:51])[C@:43]([OH:48])([C:44]([O:46][CH3:47])=[O:45])[C@@H:32]5[N:31]([CH3:55])[C:26]4=[CH:27][C:28]=3[O:29][CH3:30])[CH:39]=[CH:40][CH2:41][N:36]7[CH2:35][CH2:34]6)[CH2:18]1)[CH2:4]2.OS(O)(=O)=O>O>[CH3:1][CH2:2][C@@:3]12[O:22][C@@H:21]1[C@H:19]1[CH2:20][N:5]([CH2:6][CH2:7][C:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[NH:15][C:16]=3[C@@:17]([C:56]([O:58][CH3:59])=[O:57])([C:23]3[CH:24]=[C:25]4[C@:33]56[C@@H:37]7[C@:38]([CH2:53][CH3:54])([C@@H:42]([O:49][C:50]([CH3:52])=[O:51])[C@:43]([OH:48])([C:44]([O:46][CH3:47])=[O:45])[C@@H:32]5[N:31]([CH3:55])[C:26]4=[CH:27][C:28]=3[O:29][CH3:30])[CH:39]=[CH:40][CH2:41][N:36]7[CH2:35][CH2:34]6)[CH2:18]1)[CH2:4]2

Participants

3

Reactant 1

HCID 259897Leurosine sulfate

Product 1

HCID 442111methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 0.25 g. of leurosine sulfate were converted to the free base by dissolving the salt in water and making the resulting solution alkaline. The free base was insoluble in the aqueous alkaline layer and was extracted with chloroform. Evaporation of the chloroform yielded leurosine free base as a residue.

Workup

  1. extractionwas extracted with chloroform
  2. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-580e176d2e18422ea17dc317244860dc
Source dataset
uspto-grants-1980_03
Patent number
US04191688

Reaction notes

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