Diethylamine → (1E,4S,4aR,5R,6aS,7S,9aR)-1-[(diethylamino)methylene]-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetate

HRID 1445976Notes

Reaction equation

HRID 1445976 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].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>C(Cl)Cl.C(OCC)(=O)C>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]\[N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])/[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[C:20]([OH:19])[C:21](=[O:22])[C:13]=2[C@H:8]2[C@@:7]([CH3:31])([C@@H:11]([OH:12])[CH2:10][CH2:9]2)[CH2:6]1)(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 24807978(1E,4S,4aR,5R,6aS,7S,9aR)-1-[(diethylamino)methylene]-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetateYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 50 mg (0.116 mmol) 17-hydroxywortmannin in 1 mL CH2Cl2 is added 22.5 mL (0.217 mmol) diethylamine. The reaction mixture is stirred at room temperature for 2 hours 30 minutes and then concentrated in vacuo to give an orange paste. The residue is dissolved in ethyl actate (EtOAc) and precipitated with hexane. The precipitate is washed two times with hexane to give 45 mg (77%) product as an orange solid. HRMS (ESI) m/z calcd for C27 H37NO8 503.25206, found: 504.25747 (M+H)+1.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an orange paste
  3. customprecipitated with hexane
  4. washThe precipitate is washed two times with hexane

Sources & evidence

ORD record
ord-1d595345824e4075818254a7559eafac
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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