Dichloromethane → HCID 68541862, compound

HRID 1445984Notes

Reaction equation

HRID 1445984 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=C[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].[CH:32]1([NH:38][CH3:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[CH2:40](Cl)Cl>>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:39]\[N:38]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[CH3:40])/[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[CH:8]2[C@@:7]([CH3:31])([C@@H:11]([OH:12])[CH2:10][CH2:9]2)[CH2:6]1)(=[O:3])[CH3:1]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7514N-MethylcyclohexylamineHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 68541862HCID 68541862, compoundYield 46%

Procedure

To a solution of 50 mg (0.12 mmol) 17-hydroxywortmannin in 0.5 mL CH2Cl2 is added 27.2 mg (0.24 mmol) cyclohexyl-methyl-amine. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with Et2O to give 30 mg (46%) product as an orange powder. MS (ESI) m/z 544.25 (M+1).

Workup

  1. customCH2Cl2 is removed in vacuo
  2. customThe residue is triturated with Et2O

Sources & evidence

ORD record
ord-5cec49186997435da892c9b3e1c28462
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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