Potassium Carbonate → tert-butyl 2-[3,5-dimethyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenoxy]acetate

HRID 2216142Notes

Reaction equation

HRID 2216142 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[C:10]([O:14][C:15](=[O:44])[NH:16][C:17]([C:19]1[S:20][C:21]([S:42][CH3:43])=[C:22]([S:24]([C:27]2[CH:28]=[C:29]([C:33]3[C:38]([CH3:39])=[CH:37][C:36]([OH:40])=[CH:35][C:34]=3[CH3:41])[CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:23]=1)=[NH:18])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:40][C:36]1[CH:35]=[C:34]([CH3:41])[C:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([S:24]([C:22]3[CH:23]=[C:19]([C:17]([NH:16][C:15]([O:14][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:44])=[NH:18])[S:20][C:21]=3[S:42][CH3:43])(=[O:26])=[O:25])[CH:28]=2)=[C:38]([CH3:39])[CH:37]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 145857620tert-butyl N-[4-[3-(4-hydroxy-2,6-dimethylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857690tert-butyl 2-[3,5-dimethyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenoxy]acetateYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Bromo-acetic acid tert-butyl ester (0.013 mL, 0.085 mmol) was added dropwise to a solution of {[4-(4′-hydroxy-2′,6′-dimethyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.050 g, 0.077 mmol) [example 124, step b] and potassium carbonate (0.021 g, 0.154 mmol) in acetone [1 mL] at room temperature and stirred for 18 hours. The reaction was evaporated and column chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (0.011 g, 28%) as a solid. ESI-MS (m/z): Calcd. for C31H38N2O7S3: 646.18; found: 646.8.

Workup

  1. customThe reaction was evaporated

Sources & evidence

ORD record
ord-c0ed712f929148728bfc62c061250b3a
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

Loading…