Triethylamine → N-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-methoxyphenyl]-N-methylcarbamic Acid t-butyl Ester

HRID 353490Notes

Reaction equation

HRID 353490 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH2:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[O:19]=[C:20]1[NH:24][C:23](=[O:25])[CH:22]([CH2:26][C:27]2[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=2)[S:21]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH:17][C:33](=[O:34])[CH2:32][O:31][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH:22]2[S:21][C:20](=[O:19])[NH:24][C:23]2=[O:25])=[CH:37][CH:36]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10198914tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid

Product 1

HCID 9936338N-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-methoxyphenyl]-N-methylcarbamic Acid t-butyl EsterYield 85.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension at 0° C. of N-(2-amino-5-methoxyphenyl)-N-methylcarbamic acid t-butyl ester (4.2 g) and 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (5.2 g) in methylene chloride (30 ml) was added triethylamine (5.1 ml) and 50% propylphosphonic acid cyclic anhydride in ethyl acetate (12.7 g) and the mixture was stirred at the same temperature for 2 hours. At the end of this time to the reaction mixture was added 5% aqueous sodium hydrogencarbonate solution and the mixture was extracted with methylene chloride. The extract was washed with water and diluted hydrochloric acid and concentrated in vacuo. To the residue was added methanol (40 ml) and the precipitated crystals were filtered to give the title compound (7.3 g, yield 85%).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water and diluted hydrochloric acid
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added methanol (40 ml)
  5. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-4443f8c714e04a14b0561ca5329211d7
Source dataset
uspto-grants-2004_06
Patent number
US06753347B2

Reaction notes

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