Ethyl diazoacetate → HCID 178438680, compound

HRID 1412306Notes

Reaction equation

HRID 1412306 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]3[N:33]=[CH:34][N:35]=[C:9]23)[CH2:4][CH2:3]1.[N+](=[CH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[N-]>C([O-])(=O)C.[Rh+].C(Cl)Cl>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]#[N:29])=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]3[N:33]=[CH:34][N:35]=[C:9]23)[CH2:4][CH2:3]1)[CH3:43]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 178438592HCID 178438592, compound

Product 1

HCID 178438680HCID 178438680, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178476747HCID 178476747, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-{[4-(trans-4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1 g), rhodium(I) acetate (0.023 g) and methylene chloride (10 mL) was added dropwise ethyl diazoacetate (0.64 mL) at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound as a colorless solid (0.68 g, 59%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3b454bb0496d4d10be4110cc4d2fd06b
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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