Water → HCID 68542308, compound

HRID 1446022Notes

Reaction equation

HRID 1446022 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].Cl.[CH2:33]([NH2:35])[CH3:34].C(N(CC)CC)C.O>C(Cl)Cl>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]/[NH:35][CH2:33][CH3:34])/[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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 68542308HCID 68542308, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.23 mmol) 17-hydroxywortmannin in 2 mL CH2Cl2 is added 100 mg of ethylamine hydrochloride and 100 μL triethylamine. The reaction mixture is stirred at room temperature for 24 h. Water is added and the CH2Cl2 is removed, filtered through K2CO3 and concentrated in vacuo. The residue is dissolved in EtOAc and precipitated with hexanes to give a yellow powder (32 mg, 29%). MS (ESI) m/z 476.22813 (M+1).

Workup

  1. customthe CH2Cl2 is removed
  2. filtrationfiltered through K2CO3
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in EtOAc
  5. customprecipitated with hexanes

Sources & evidence

ORD record
ord-78f317cec33a4f32a9da1b769f45cddc
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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