Triethylamine → HCID 68542429, compound

HRID 1446001Notes

Reaction equation

HRID 1446001 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(N(CC)CC)C.Cl.[N:40]12[CH2:48][C:44]([CH2:49][NH:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([CH2:45][CH2:46][CH2:47]1)[CH2:43][CH2:42][CH2:41]2>C(Cl)Cl>[N:40]12[CH2:48][C:44]([CH2:49][N:50]([CH:18]=[C:17]3[C:16]4[C:15]([CH3:30])([C:14]5[CH:5]([O:4][C:2](=[O:3])[CH3:1])[CH2:6][C:7]6([CH3:31])[CH:8]([C:13]=5[C:21](=[O:22])[C:20]=4[OH:19])[CH2:9][CH2:10][CH:11]6[OH:12])[CH:26]([CH2:27][O:28][CH3:29])[O:25][C:23]3=[O:24])[CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)([CH2:43][CH2:42][CH2:41]1)[CH2:45][CH2:46][CH2:47]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 986734017beta-Hydroxy wortmanninHCID 68544496HCID 68544496, compound

Product 1

HCID 68542429HCID 68542429, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.23 mmol) 17-hydroxywortmannin and triethylamine (65 μL, 0.46 mmol) in 2 mL CH2Cl2 is added (1-aza-bicyclo[3.3.1]non-5-ylmethyl)-benzyl-amine hydrochloride (114 mg). 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 676 (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-c87d315cddf2484686626e02f595700c
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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