Lithium Chloride → (13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

HRID 618589Notes

Reaction equation

HRID 618589 reaction equation
[CH3:1][C@H:2]1[C:20](=[O:21])[O:19][C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:17])[O:15][C@H:14]([C@@H:26]([C@@H:28]([OH:37])[C@@H:29](Cl)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][C@H:7]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([Cl:47])[CH:40]=2)[C:5](=[O:6])[NH:4][CH2:3]1.[Li+].[Cl-]>CC(C)=O>[CH3:1][CH:2]1[C:20](=[O:21])[O:19][CH:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:17])[O:15][CH:14]([CH:26]([CH:28]2[O:37][CH:29]2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][CH:7]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([Cl:47])[CH:40]=2)[C:5](=[O:6])[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 9918016Cryptophycin 8

Product 1

HCID 5468287(13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetroneYield 35.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Cryptophycin 8 (20 mg) in 1.0 mL of dry acetone(distilled from K2CO3) was added 20 mg of LiCl. The mixture was stirred for 3 days at 100° C., cooled to room temperature, and evaporated. The residue was subjected to reversed-phase HPLC using 82/18 MeOH/H2O to give Cryptophycin 27 (6.8 mg) and recovered Cryptophycin 8 (10.1 mg).

Workup

  1. temperaturecooled to room temperature
  2. customevaporated

Sources & evidence

ORD record
ord-d79e2bd748ff473bbc55cbb9dcc2a9f0
Source dataset
uspto-grants-1999_09
Patent number
US05952298

Reaction notes

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