Potassium Carbonate → HCID 9852601, compound

HRID 618590Notes

Reaction equation

HRID 618590 reaction equation
[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:30][CH:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][CH:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C@H:2]1[C:20](=[O:21])[O:19][C@@H:18]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:16](=[O:17])[O:15][C@H:14]([C@@H:26]([C@H:28]2[O:30][C@H:29]2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][C@H:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 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-tetrone

Product 1

HCID 9852601HCID 9852601, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Cryptophycin 27 (6.0 mg) in 1.0 mL of dry acetone was treated with 15 mg of potassium carbonate at 85° C. After 24 h the reaction mixture was filtered and the filtrate was evaporated. The residue was subjected to normal-phase HPLC on silica using 50/50 EtOAc/hexane to give Cryptophycin 39 (3.2 mg).

Workup

  1. filtrationAfter 24 h the reaction mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a6c522e7248d4f8590ecf78ab89dfcbe
Source dataset
uspto-grants-1999_09
Patent number
US05952298

Reaction notes

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