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Glycine ethyl ester, hydrochloride → Ethyl [2-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]-acetylamino]acetate

HRID 229592
Notes
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Reaction equation

HRID 229592 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:29][CH3:30])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][C:16]=2[O:17][CH2:18][C:19](O)=[O:20])(=[O:11])=[O:10])[CH:8]=1)#[N:2].Cl.[CH2:32]([O:34][C:35](=[O:38])[CH2:36][NH2:37])[CH3:33].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O.C(N(CC)CC)C>[CH2:32]([O:34][C:35](=[O:38])[CH2:36][NH:37][C:19](=[O:20])[CH2:18][O:17][C:16]1[CH:22]=[C:23]([CH:26]([CH3:28])[CH3:27])[CH:24]=[CH:25][C:15]=1[CH2:14][CH2:13][NH:12][S:9]([C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[O:29][CH3:30])(=[O:10])=[O:11])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18456942[2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid

Product 1

HCID 18456978
Ethyl [2-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]-acetylamino]acetate
Yield 91.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 0.3 g of [2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid, 0.107 g of glycine ethyl ester hydrochloride and 0.103 g of 1-hydroxybenzotriazole monohydrate in N,N-dimethylformamide were added 0.106 mL of triethylamine and 0.146 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride under ice-cooling, and the mixture was stirred at room temperature for 15 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium bicarbonate solution, water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetatehexane) to give 0.33 g of ethyl[2-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetylamino]acetate

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium bicarbonate solution, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetatehexane)

Sources & evidence

ORD record
ord-1dfb2ee9c86147fd9388848a0cd10f56
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07563822B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes