3-(Benzylamino)propionitrile → Acetic acid 4-{[benzyl-(2-cyano-ethyl)-amino]-methylene}-6,17-dihydroxy-1-methoxymethyl-10,13-dimethyl-3,7-dioxo-1,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

HRID 1446011Notes

Reaction equation

HRID 1446011 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:39][CH2:40][CH2:41][C:42]#[N:43])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[CH2:32]([N:39]([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])[CH2:40][CH2:41][C:42]#[N:43])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 697193-(Benzylamino)propionitrileHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 68541487Acetic acid 4-{[benzyl-(2-cyano-ethyl)-amino]-methylene}-6,17-dihydroxy-1-methoxymethyl-10,13-dimethyl-3,7-dioxo-1,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.23 mmol) 17-hydroxywortmannin in 2 mL CH2Cl2 is added 3-benzylamino-propionitrile (73 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 592 (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-9fca3092b9324c28923b67d68dcdfe10
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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