17beta-Hydroxy wortmannin → HCID 68538614, compound

HRID 1445996Notes

Reaction equation

HRID 1445996 reaction equation
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[CH3:32][O:33][C:34](=[O:44])[C:35]([CH3:43])=[CH:36][CH:37]([NH:41][CH3:42])[CH:38]([CH3:40])[CH3:39]>C(Cl)Cl>[CH3:32][O:33][C:34](=[O:44])[C:35]([CH3:43])=[CH:36][CH:37]([N:41]([CH:18]=[C:17]1[C:16]2[C:15]([CH3:30])([C:14]3[CH:5]([O:4][C:2](=[O:3])[CH3:1])[CH2:6][C:7]4([CH3:31])[CH:8]([C:13]=3[C:21](=[O:22])[C:20]=2[OH:19])[CH2:9][CH2:10][CH:11]4[OH:12])[CH:26]([CH2:27][O:28][CH3:29])[O:25][C:23]1=[O:24])[CH3:42])[CH:38]([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 986734017beta-Hydroxy wortmanninHCID 86239014HCID 86239014, compound

Product 1

HCID 68538614HCID 68538614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.23 mmol) 17-hydroxywortmannin in 2 mL CH2Cl2 is added 2,5-dimethyl-4-methylamino-hex-2-enoic acid methyl ester (86 mg, 0.46 mmol). The reaction mixture is stirred at room temperature for 12 hours and then concentrated in vacuo. The residue is dissolved in EtOAc and precipitated with hexane. The precipitate is washed two times with hexane to give the product as a yellow solid. MS (ESI) m/z 630 (M+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. customprecipitated with hexane
  4. washThe precipitate is washed two times with hexane

Sources & evidence

ORD record
ord-e0024477ae4c441fbd6d249fce219ac2
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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