Acetyl chloride → (+,-) Trans N-(2-{4'-[2-(Propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide

HRID 989494Notes

Reaction equation

HRID 989494 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[CH3:26][CH:25]([S:22]([NH:21][C@@H:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][C:35](=[O:37])[CH3:36])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)(=[O:24])=[O:23])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69112967(+,-) Trans Propane-2-sulfonic Acid {2-[4'-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide

Product 1

HCID 69113096(+,-) Trans N-(2-{4'-[2-(Propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(+,−) Trans propane-2-sulfonic acid {2-[4′-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide (prepared in example 9) was dissolved in 20 mL of dry methylene chloride and triethylamine added (0.275 mL, 1.98 mmol). To this stirred mixture was added acetyl chloride (0.084 mL, 1.19 mmol). The reaction was stirred at room temperature for 3 days. The reaction was concentrated in vacuo and chromatographed on a Chromatotron® eluting with 98:2 methylene chloride:methanol which afforded 150 mg (64% 2 steps) of the title compound. The NMR was consistent with the assigned structure.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customchromatographed on a Chromatotron®
  3. washeluting with 98:2 methylene chloride

Sources & evidence

ORD record
ord-8fdec11e57b74e7fb542d1b1d4f702aa
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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