Ethanethiol → HCID 178477504, compound

HRID 1714405Notes

Reaction equation

HRID 1714405 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][C:21](O)=[O:22])[CH2:16][CH2:15]2)=[O:12])=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:30]([SH:32])[CH3:31].C([Li])CCC.C([O-])(O)=O.[Na+]>ClCCl.C(COC)OC>[CH2:30]([S:32][C:21](=[O:22])[CH2:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)=[O:12])[CH2:19][CH2:18]1)[CH3:31]

Participants

8

Reactant 5

HCID 6343EthanethiolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 178418339ButyllithiumHCID 178525567HCID 178525567, compound

Product 1

HCID 178477504HCID 178477504, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.19 g of Trans-{4-[(Quinoline-4-carbonyl)-amino]-cyclohexyl}-acetic acid (7 mmol) was added in 1300 mL of dichloromethane. Then 1.8 mL of oxalyl chloride was added (21 mmol). The suspension was heated to reflux for 3 hours and then the cloudy mixture was concentrated under vacuum. The residue was taken up in 500 mL of dichloromethane as a suspension and (1.28 g, 21 mmol) sodium ethylthiolate freshly prepared from 1.45 mL of ethanothiol and 12.07 mL of butyl lithium (1.6 M in toluene) at 0° C. and by stirring in dimethoxyethane (20 mL) for 1 hour at room temperature. The reaction mixture was stirred overnight. NaHCO3 was added and the organic phase was extracted three times with dichloromethane. The organic phases were dried and concentrated and the residue was chromatographed with heptane/ethyl acetate 1:1 to yield the title compound as a solid (1.97 g, 78.9% yield). MS (m/e): 357.3 (M+H+).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 3 hours
  3. concentrationthe cloudy mixture was concentrated under vacuum
  4. extractionthe organic phase was extracted three times with dichloromethane
  5. customThe organic phases were dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed with heptane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-ae6fcda19168494a9b2ba5a39bed13ad
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

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