Triethylamine → HCID 23513855, compound

HRID 278358Notes

Reaction equation

HRID 278358 reaction equation
[CH3:1][O:2][C:3]([C:5]1([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](Cl)=[O:38].CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([S:11]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9][N:8]([C:37]([C:33]3[S:32][CH:36]=[CH:35][CH:34]=3)=[O:38])[CH2:7][CH2:6]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1)[C:22]#[C:23][CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 789282-Thiophenecarbonyl chlorideHCID 54136994HCID 54136994, compound

Product 1

HCID 23513855HCID 23513855, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-but-2-ynyloxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (500 mg, 1.29 mmol) in methylene chloride (10 ml) was added triethylamine (261 mg, 2.58 mmol), thiophenylcarbonyl chloride (227 mg, 1.55 mmol) followed by a catalytic amount of dimethylaminopyridine. The resulting mixture was stirred for 15 hours at room temperature, quenched with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 480 mg (81%) of the product as a solid. HR-MS: m/z Calculated for C22H23NO6S2 462.1040; Found 462.1039.

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3bf06c004bad40089301be0f45f0ac16
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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