Triethylamine → HCID 18612925, compound

HRID 1420606Notes

Reaction equation

HRID 1420606 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]([CH2:11]O)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[O:35]([CH2:42][C:43](Cl)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:5]([CH2:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=2[NH:1][C:43](=[O:44])[CH2:42][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8])(=[O:14])=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 18612758Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate

Product 1

HCID 18612925HCID 18612925, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) mixture of 1.5 g (3.8 mmol) of methyl 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate and 2.7 ml (19 mmol) of triethylamine in 15 ml of CH2Cl2 was added 1.58 g (11.4 mol) of phenoxyacetyl chloride. The mixture was stirred at room temperature overnight and filtered. The filtrate was washed with H2O, 2 N citric acid, and brine and dried with Na2SO4. The solvent was removed to give 2.4 g of crude methyl 2-{(4-methoxybenzenesulfonyl)-[2-(phenoxyacetylamino)benzyl]amino}acrylate as an oil. Anal. for C26H26N2O7S: Calc'd: C,61.2; H,5.1; N,5.5; Found: C,62.6; H,5.1; N,4.0; Mass spectrum (ES) 511 (M+H).

Workup

  1. temperatureTo a cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, 2 N citric acid, and brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e2954bf217c9400f885b164802911f56
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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