Ethyl diazoacetate → HCID 15838327, compound

HRID 1938920Notes

Reaction equation

HRID 1938920 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-8f46bf793931468795b6e14c1f74b272
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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