Triethylamine → Methyl 2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]acrylate

HRID 1420597Notes

Reaction equation

HRID 1420597 reaction equation
C(O[CH2:5][CH:6]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]([C:34](=[O:36])[CH3:35])[C:31](=[O:33])[CH3:32])[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:7]([O:9][CH3:10])=[O:8])(=O)C.C(N(CC)CC)C>C(Cl)Cl>[C:31]([N:30]([C:34](=[O:36])[CH3:35])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[C:6](=[CH2:5])[C:7]([O:9][CH3:10])=[O:8])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18613025Methyl 3-acetoxy-2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]propionate

Product 1

HCID 18612823Methyl 2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.0 g (1.97 mmol) of methyl 3-acetoxy-2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]propionate and 0.826 ml (5.92 mmol) of triethylamine in 5 ml of CH2Cl2 was stirred at room temperature overnight. The solution was diluted with 30 ml of CH2Cl2 and washed with 20 ml each of H2O, 2 N citric acid, brine and dried with Na2SO4. The solvent was removed under vacuum to give a brown oil. Anal. for C22H24N2O7S: Calc'd: C,57.4; H,5.3; N,6.1; S,7.0; Found: C,56.2; H,5.5; N,5.6; S,7.2.

Workup

  1. washwashed with 20 ml each of H2O, 2 N citric acid, brine
  2. dry with materialdried with Na2SO4
  3. customThe solvent was removed under vacuum
  4. customto give a brown oil

Sources & evidence

ORD record
ord-80098c2c07e243a98bcf84ad9643092b
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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