Pyridine → HCID 69745341, compound

HRID 1063912Notes

Reaction equation

HRID 1063912 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C@:14]3([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].N1C=CC=CC=1.[CH2:37]([S:40](Cl)(=[O:42])=[O:41])[CH2:38][CH3:39]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([C@:14]3([CH2:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][N:17]([S:40]([CH2:37][CH2:38][CH3:39])(=[O:42])=[O:41])[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 69745125HCID 69745125, compound

Product 1

HCID 69745341HCID 69745341, compoundYield 39,919.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (7.91 g) and pyridine (30 ml) in chloroform (15 ml) was added a solution of propanesulfonyl chloride (5.02 mg) in chloroform (15 ml) at 0° C. The resulting mixture was stirred for 3 hours at 0° C. Ethyl acetate (200 ml) was added and the solution was washed with 1N hydrochloric acid (150 ml) for two times, saturated sodium bicarbonate, and brine, dried over magnesium sulfate and evaporated to give a brown gum. The gum was dissolved in ethyl acetate (75 ml) and silica gel (12 ml) was added to the solution. The silica gel was removed by filtration, and the resulting filtrate was evaporated. Silica gel column chromatography (eluent: ethyl acetate/hexane from 13/27 to 9/11) afforded tert-butyl 2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-propanesulfonyl-1,4-thiazepin-7-yl]acetate (7.81 g) as an yellowish solid.

Workup

  1. washthe solution was washed with 1N hydrochloric acid (150 ml) for two times, saturated sodium bicarbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a brown gum
  5. additionsilica gel (12 ml) was added to the solution
  6. customThe silica gel was removed by filtration
  7. customthe resulting filtrate was evaporated

Sources & evidence

ORD record
ord-ec15cc212daf4c948e49e8ccc21bb06b
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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