Ethyl Acetate → HCID 89515290, compound

HRID 1411106Notes

Reaction equation

HRID 1411106 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C@@H:15]3[CH2:21][C:18]4([CH2:20][CH2:19]4)[CH2:17][N:16]3[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:12][C:11]=2[CH:29]=1)(C)C.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CO>[C:6]([C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C@@H:15]3[CH2:21][C:18]4([CH2:19][CH2:20]4)[CH2:17][N:16]3[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[NH:12][C:11]=2[CH:29]=1)#[CH:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 89515398HCID 89515398, compound

Product 1

HCID 89515290HCID 89515290, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A brown opaque mixture of (S)-tert-butyl 6-(6-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate (0.99 kg, 2.41 mol, 1 equiv.) in methanol (5.5 L) is treated with solid potassium carbonate (340 g, 2.46 mol, 1.02 equiv.) for about 1.5 hours and the reaction was complete as indicated by TLC/MS. The mixture was rotavapped and solvent swapped to EtOAc (6 L), and then washed with 10% NaCl solution (5 L). Upon drying over Na2SO4 it was rotavapped and vacuum dried at about 25˜30° C. overnight to afford 0.845 kg (104% yield, 98% HPLC purity) of the title compound as a light brown foam. ESI MS m/z (M+H)+ 338.19.

Workup

  1. washwashed with 10% NaCl solution (5 L)
  2. dry with materialUpon drying over Na2SO4 it
  3. customvacuum dried at about 25˜30° C. overnight

Sources & evidence

ORD record
ord-097db17344f847239a84bc642334b4a5
Source dataset
uspto-grants-2014_12
Patent number
US08921573B2

Reaction notes

Loading…