Acetic Acid → HCID 45092164, compound

HRID 1371397Notes

Reaction equation

HRID 1371397 reaction equation
[NH:1]1[C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][N:3]=[N:2]1.[CH3:15][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>ClCCl.CO.CCCCCC>[CH3:15][N:3]1[N:2]=[N:1][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[N:4]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 178453125HCID 178453125, compound

Product 1

HCID 45092164HCID 45092164, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of Intermediate 36 (1.0 g) in dichloromethane (35 ml) and methanol (10 ml) at 22° C. under nitrogen was added dropwise 10% trimethylsilyldiazomethane in hexane (12.0 ml). The mixture was stirred for 2 h at 22° C. before acetic acid (2 ml) was added dropwise and the solvents were evaporated in vacuo. The crude residue was purified by Biotage flash column chromatography on silica gel (90 g cartridge), eluting with 10% cyclohexane in ether. The fractions for the first eluting isomer were combined and the solvents evaporated in vacuo to give the title compound as pale yellow crystals (0.487 g).

Workup

  1. additionwas added dropwise
  2. customthe solvents were evaporated in vacuo
  3. customThe crude residue was purified by Biotage flash column chromatography on silica gel (90 g cartridge)
  4. washeluting with 10% cyclohexane in ether
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-27f7ed00f80a407893cbe9d582ebb1e4
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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