Phosphoric Acid → Paclitaxel

HRID 1955487Notes

Reaction equation

HRID 1955487 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].C(#N)C.P(=O)(O)(O)O>O>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[CH3:38]/[CH:39]=[C:34](/[C:32]([NH:31][C@H:24]([C@@H:23]([OH:40])[C:21]([O:20][C@@H:19]1[C:2]([CH3:1])=[C:3]2[C:15]([CH3:16])([CH3:17])[C@:14]([OH:41])([C@@H:13]([O:42][C:43]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:44])[C@@H:12]3[C@:11]4([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]4[CH2:9][C@H:8]([OH:57])[C@@:7]3([CH3:58])[C:5]([C@@H:4]2[O:59][C:60]([CH3:62])=[O:61])=[O:6])[CH2:18]1)=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:33])\[CH3:35]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 6342AcetonitrileHCID 36314Paclitaxel

Product 2

HCID 36314PaclitaxelHCID 6436208Cephalomannine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

HPLC analysis for paclitaxel content in liposome formulations was performed on a 15 cm long pentafluorophenyl (PFP) column (ES Industries, Inc.) with a Waters 501 HPLC pump and a Waters 991 photodiode array detector. The flow rate and temperature were controlled at 1.5 ml/min. and 27° C., respectively. The mobile phase consisted of 44% acetonitrile, 56% water, and about 0.1% (vol.) of phosphoric acid. This system gave retention times for paclitaxel and cephalomannine around 12.5 and 9.5 minutes, respectively, with UV detection at 228 nm. The HPLC chromatogram of the paclitaxel/cephalomannine (taxoid) mixture is presented in FIG. 7.

Workup

  1. customwere controlled at 1.5 ml/min. and 27° C.

Sources & evidence

ORD record
ord-692bf33ad7c94670a36d1b0ca48f06fe
Source dataset
uspto-grants-1998_07
Patent number
US05776486

Reaction notes

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