Water → HCID 131735416, compound

HRID 631179Notes

Reaction equation

HRID 631179 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.N1C=CC=CC=1.ClCCl.O.[CH3:18][C:19]1[C@@H:36]([O:37][C:38]([C@H:40]([OH:57])[C@@H:41]([NH:48][C:49]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[O:50])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[CH2:35][C@:31]2([OH:58])[C:32]([CH3:34])([CH3:33])[C:20]=1[C@@H:21]([O:76][C:77]([CH3:79])=[O:78])[C:22]([C@@:24]1([CH3:75])[C@H:29]([C@@H:30]2[O:59][C:60]([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:61])[C@:28]2([O:70][C:71]([CH3:73])=[O:72])[CH2:68][O:69][C@@H:27]2[CH2:26][C@@H:25]1[OH:74])=[O:23]>CN(C)C1C=CN=CC=1.CCCCCC>[CH3:18][C:19]1[C@@H:36]([O:37][C:38]([C@H:40]([OH:57])[C@@H:41]([NH:48][C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:50])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[CH2:35][C@:31]2([OH:58])[C:32]([CH3:33])([CH3:34])[C:20]=1[C@@H:21]([O:76][C:77]([CH3:79])=[O:78])[C:22]([C@@:24]1([CH3:75])[C@H:29]([C@@H:30]2[O:59][C:60]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:61])[C@:28]2([O:70][C:71]([CH3:73])=[O:72])[CH2:68][O:69][C@@H:27]2[CH2:26][C@@H:25]1[OH:74])=[O:23].[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 36314Paclitaxel2×

Product 1

HCID 131735416HCID 131735416, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

In order to form a functional group which may be conjugated to PLL in paclitaxel (PTX), PTX, succinic anhydride (SA) and 4-dimethylaminopyridine (DMAP) were put into a pyridine solution, and then were reacted for 3 hours. After 3 hours, the reaction solution was mixed with dichloromethane such that a volume ratio therebetween was 1:1, the reaction solution was put into a separatory funnel with water, and thereby a remaining material after the reaction was removed. A solution obtained from the separatory funnel was deposited in a hexane to obtain PTX-SA.

Workup

  1. customIn order to form a functional group which
  2. customwere reacted for 3 hours
  3. customa remaining material after the reaction was removed
  4. customA solution obtained from the separatory funnel

Sources & evidence

ORD record
ord-3f996af8858c4c07be5866958b780085
Source dataset
uspto-grants-2016_04
Patent number
US09320809B2

Reaction notes

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