Ethyl diazoacetate → HCID 15838327, compound

HRID 1735155Notes

Reaction equation

HRID 1735155 reaction equation
[C:1]([N:9]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:10]1=[CH:11][CH2:12][C@@H:13]1[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[OH:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N-]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][O:29][C@H:17]1[CH2:16][CH2:15][C@H:14]2[C@H:13]3[C@H:22]([CH2:21][CH2:20][C@:18]12[CH3:19])[C@:23]1([CH3:28])[C:10]([N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:26](=[O:27])[CH2:25][CH2:24]1)=[CH:11][CH2:12]3)[CH3:37]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 15838326HCID 15838326, compound

Product 1

HCID 15838327HCID 15838327, compound

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To the alcohol product from Step B, above and ethyl diazoacetate (0.5 ml) in methylene chloride (6.5 ml) was added rhodium diacetate dimer (15 mg) intermittently during 2 hours. The mixture was stirred at room temperature for 18 hours. The mixture was concentrated and the residue was purified via preparative TLC using two silica gel plates (2000μ) developed with 40% EtOAc in hexanes to afford the title compound (Rf =0.33).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified via preparative TLC

Sources & evidence

ORD record
ord-0ec204933b5d42a7ad808ea59eee2f88
Source dataset
uspto-grants-1996_07
Patent number
US05536727

Reaction notes

Loading…