17beta-Hydroxy wortmannin → HCID 68544627, compound

HRID 1446000Notes

Reaction equation

HRID 1446000 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].[C:32]1([S:38]([CH2:41][CH2:42][NH:43][CH2:44][CH2:45][CH2:46][N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:32]1([S:38]([CH2:41][CH2:42][N:43]([CH:18]=[C:17]2[C:16]3[C:15]([CH3:30])([C:14]4[CH:5]([O:4][C:2](=[O:3])[CH3:1])[CH2:6][C:7]5([CH3:31])[CH:8]([C:13]=4[C:21](=[O:22])[C:20]=3[OH:19])[CH2:9][CH2:10][CH:11]5[OH:12])[CH:26]([CH2:27][O:28][CH3:29])[O:25][C:23]2=[O:24])[CH2:44][CH2:45][CH2:46][N:47]([CH2:48][CH3:49])[CH2:50][CH3:51])(=[O:40])=[O:39])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 986734017beta-Hydroxy wortmanninHCID 14855222N~3~-[2-(Benzenesulfonyl)ethyl]-N~1~,N~1~-diethylpropane-1,3-diamine

Product 1

HCID 68544627HCID 68544627, 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 N′-(2-benzenesulfonyl-ethyl)-N,N-diethyl-propane-1,3-diamine (139 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 730 (M+H).

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-bb9eaacb0a35406ea2d26a9d53db2aa5
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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