Triethylamine → Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

HRID 2746

Reaction equation

HRID 2746 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:4]1=[O:17].[S:18]1[C:22]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][C:20]2[CH:27]=[CH:28][CH:29]=[CH:30][C:19]1=2.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[C:12]([C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[CH2:8][N:5]1[CH2:6][CH2:7][C@H:3]([NH:2][S:23]([C:22]2[S:18][C:19]3[CH:30]=[CH:29][CH:28]=[CH:27][C:20]=3[CH:21]=2)(=[O:24])=[O:25])[C:4]1=[O:17])#[N:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27763331-Benzothiophene-2-sulfonyl chlorideHCID 228707863-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

Product 1

HCID 15886959Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amideYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride (0.36 g, 1.43 mmol) in 15 mL of CH2Cl2 is added benzo[b]thiophene-2-sulfonyl chloride (0.32 g, 1.38 mmol). To the resulting solution is added triethylamine (0.29 g, 2.88 mmol). After 16 h, the solution is diluted with EtOAc. The solution is washed with 1N HCl, saturated NaHCO3, and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The title compound (0.45 g, 1.09 mmol) is obtained as white solid.

Workup

  1. washThe solution is washed with 1N HCl, saturated NaHCO3, and saturated NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e191b19e3934f0d93b05d666f8a5d42
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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