Ethyl propiolate → HCID 54535752, compound

HRID 1953232Notes

Reaction equation

HRID 1953232 reaction equation
[C:1]([O:5][C:6]([C:8]1([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:49]([O:53][CH2:54][CH3:55])(=[O:52])[C:50]#[CH:51]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1([N:13]([CH:51]=[CH:50][C:49]([O:53][CH2:54][CH3:55])=[O:52])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 12182Ethyl propiolateHCID 2724141Tetrabutylammonium FluorideHCID 54290816HCID 54290816, compound

Product 1

HCID 54535752HCID 54535752, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[4-(4-fluoro-phenoxy)-benzenesulfonylamino]-cyclopentanecarboxylic acid tert-butyl ester (1.0 g, 2.3 mmole) in 10 mL THF and 2.3 mL (2.3 mmole) 1M tetrabutylammonium fluoride in THF was added 0.23 mL (2.3 mmole) ethyl propiolate at ambient temperature. After stirring 1 hour the reaction was complete by HPLC and was stripped to dryness in vacuo. The residue was dissolved in 20 mL ethyl acetate and washed with 2×10 mL water and the organic solution stripped to an oil. This oil was chromatographed over silica gel, eluting with 10% ethyl acetate/hexane to yield 0.95 g (77% yield) 1-{(2-ethoxycarbonyl-vinyl)-[4-(4-fluoro-phenoxy)-benzenesulfonyl]-amino}-cyclopentanecarboxylic acid tert-butyl ester as a colorless oil. 1H NMR (CDCl3) indicated a 1.5:1 trans/cis ratio.

Workup

  1. washwashed with 2×10 mL water
  2. customThis oil was chromatographed over silica gel
  3. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7e9d6960a11c4976aca8a4111095c0ca
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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