Water → HCID 68545926, compound
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].[OH2:32].C(N(CC)CC)C>C(#N)C>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]/[OH:19])/[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[C:20]([OH:32])[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
17-hydroxy-wortmannin (20 mg, 0.047 mmol) is dissolved in 4 mL acetonitrile and 2 mL water with 0.5 mL triethylamine. The reaction mixture is stirred at room temperature overnight. The title compound is isolated by preparative HPLC using Nova-Pak HRC 18, 60A, 6 um, 19×300 mm column (Waters) at UV 254 nm (Mobile Phase A is 100 ml acetonitrile with 900 ml water, and 0.2 ml trifluoroacetic acid. Mobile Phase B is 900 ml acetonitrile with 100 ml water and 0.2 ml trifluoroacetic acid. The gradient is 0-5 min at 20% B and 80% A, 5-35 min from 20% B to 70% B at flow rate 20 mL/min). The fraction at 12 min peak is collected and extracted with CH2Cl2. The organic layer is dried over anhydrous sodium sulfate and rotavaped to dryness. A total of 5 mg of yellow solid is obtained by precipitation from 1 mL CH2Cl2 and 3 mL heptane and drying using nitrogen gas and then a speecdvac. LC/MS shows [M+H] 449.31 and [M−H] 447.26.
Sources & evidence
- ORD record
- ord-0e3392c80e3e4570b27787311e9cbd5d
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666901B2
Reaction notes
Loading…