Water → HCID 178454349, compound

HRID 1875062Notes

Reaction equation

HRID 1875062 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:18][C:19]([O:22][C:23]([N:25]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:26]1[N:27](C(OC(C)(C)C)=O)[CH:28]=[C:29]([CH:31](OC)[O:32]C)[N:30]=1)=[O:24])([CH3:21])[CH3:20].O>CC(C)=O>[CH3:21][C:19]([O:22][C:23]([N:25]([C:26]1[NH:27][CH:28]=[C:29]([CH:31]=[O:32])[N:30]=1)[C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])=[O:24])([CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 684877941,1-dimethylethyl 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-[bis(methyloxy)methyl]-1H-imidazole-1-carboxylate

Product 1

HCID 178454349HCID 178454349, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A catalytic amount of pyridinium p-toluenesulfonate was added to a solution of 1,1-dimethylethyl 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-[bis(methyloxy)methyl]-1H-imidazole-1-carboxylate (1.520 g, 3.32 mmol) in acetone:water/3:2 (25 mL). The mixture was stirred at RT for 3 days. The solvent was evaporated and the residue was purified by chromatography (EtOAc:hexanes) to give 0.680 g of the title compound (0.680 g, 66%). 1H NMR (400 MHz, chloroform-d) δ ppm 10.57 (br. s., 1H), 9.57 (s, 1H), 7.61 (s, 1H), 1.51 (s, 18H). ES MS: m/z 310 (M−H), 334 (M+Na).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography (EtOAc:hexanes)

Sources & evidence

ORD record
ord-c94b73cd5c9748818a1f59ab47498fb0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…