Triethylamine → Methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzenesulfonyl)-amino}acrylate

HRID 1264599Notes

Reaction equation

HRID 1264599 reaction equation
O[CH2:2][CH:3]([N:8]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[NH2:17])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH3:36][O:37][CH2:38][C:39](Cl)=[O:40]>ClCCl>[CH3:36][O:37][CH2:38][C:39]([NH:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH2:9][N:8]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:3](=[CH2:2])[C:4]([O:6][CH3:7])=[O:5])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 18612905Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate

Product 1

HCID 18613017Methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzenesulfonyl)-amino}acrylateYield 107.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) mixture of 1.598 g (3.91 mmol) of methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate and 1.97 g (19.5) mmol) of triethylamine in 15 ml of dichloromethane was added 0.787 ml (8.60 mmol) of methoxyacetylchloride. The mixture was stirred at room temperature overnight. The mixture was then diluted with CH2Cl2 and washed with H2O, 2 N citric acid, H2O, brine and dried with Na2SO4. The solution was filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to give 1.94 g of crude methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzene-sulfonyl)-amino}acrylate as a brown oil. Mass spectrum (ES) 463.4 (M+H).

Workup

  1. temperatureTo a cooled
  2. washwashed with H2O, 2 N citric acid, H2O, brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-acd77814795e4094bf475ddbb8a63ae6
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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