Pyridine → HCID 118359521, compound

HRID 2200848Notes

Reaction equation

HRID 2200848 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH2:11][Cl:12])=[O:9].[CH3:13][C:14]1[C@@H:31]([O:32][C:33]([C@H:35]([OH:52])[C@@H:36]([NH:43][C:44]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:45])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[CH2:30][C@:26]2([OH:53])[C:27]([CH3:29])([CH3:28])[C:15]=1[C@@H:16]([O:71][C:72]([CH3:74])=[O:73])[C:17]([C@@:19]1([CH3:70])[C@H:24]([C@@H:25]2[O:54][C:55]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)=[O:56])[C@:23]2([O:65][C:66]([CH3:68])=[O:67])[CH2:63][O:64][C@@H:22]2[CH2:21][C@@H:20]1[OH:69])=[O:18]>ClCCl>[C:72]([O:71][C@@H:16]1[C:15]2[C:27]([CH3:28])([CH3:29])[C@@:26]([OH:53])([CH2:30][C@H:31]([O:32][C:33](=[O:34])[C@H:35]([O:52][C:8]([O:10][CH2:11][Cl:12])=[O:9])[C@@H:36]([NH:43][C:44](=[O:45])[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:14]=2[CH3:13])[C@@H:25]([O:54][C:55](=[O:56])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@@H:24]2[C@:23]3([O:65][C:66](=[O:67])[CH3:68])[CH2:63][O:64][C@@H:22]3[CH2:21][C@H:20]([O:69][C:8]([O:10][CH2:11][Cl:12])=[O:9])[C@@:19]2([CH3:70])[C:17]1=[O:18])(=[O:73])[CH3:74]

Participants

5

Reactant 3

HCID 1049PyridineHCID 36314PaclitaxelHCID 62754Chloromethyl chloroformate

Product 1

HCID 118359521HCID 118359521, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Pyridine (0.026 g, 23.0 mmol, 2.0 eq) was added to a solution of chloromethyl chloroformate (CMCF) [8](0.02 g, 23.0 mmol, 2.0 eq) in dry dichloromethane under an argon atmosphere at 0° C. At 0° C., a solution of paclitaxel [4114] (0.10 g, 11.7 mmol, 1.0 eq) in dry dichloromethane was added to the above reaction mixture. The reaction mixture was stirred at room temperature for 2 h. The reaction progress was monitored by TLC. After 2 h the reaction mixture was diluted with dichloromethane (25 ml), washed with a 10% solution of NaHCO3 (15 ml), brine (10 ml), and then dried over anhydrous sodium sulfate. Evaporation of the solvent under vacuum gave a white solid, [312], (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-(((chloromethoxy)carbonyl)oxy)-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4-(((chloromethoxy)carbonyl)oxy)-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate, (0.11 g, 90%)

Workup

  1. washwashed with a 10% solution of NaHCO3 (15 ml), brine (10 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-95f7b256964c4225abf423a14ed1354b
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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