Methyl isonipecotate → HCID 68540722, compound

HRID 1445994Notes

Reaction equation

HRID 1445994 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].[NH:32]1[CH2:41][CH2:40][CH:35]([C:36]([O:38][CH3:39])=[O:37])[CH2:34][CH2:33]1>C(Cl)Cl>[CH3:39][O:38][C:36]([CH:35]1[CH2:40][CH2:41][N:32]([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])[CH2:33][CH2:34]1)=[O:37]

Participants

4

Reactant 2

HCID 424914Methyl isonipecotateHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 68540722HCID 68540722, 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 methyl isonipecotate (63 μL, 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 575 (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-5c7c6bfe56504176a27245ce80298be3
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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