Hydrochloric Acid → HCID 22276399, compound

HRID 1063897Notes

Reaction equation

HRID 1063897 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[S:13](=[O:15])(=[O:14])[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]2([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[S:13](=[O:15])(=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22276396HCID 22276396, compound

Product 1

HCID 22276399HCID 22276399, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 2-[7-(5-bromo-2-thienyl)-4-tert-butoxycarbonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (5.00 g) in ethyl acetate (25 ml) was added 4N hydrochloric acid in ethyl acetate (13 ml) with ice-cooling. After stirring for 4 hours at room temperature, the mixture was poured into saturated aqueous sodium bicarbonate (50 ml). The separated organic layer was washed with brine, dried over sodium sulfate and filtered. The obtained filtrate was concentrated to give tert-butyl 2-[7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (3.03 g) as a solid.

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-2ba58dfd3b6d45e9856278e42f76ff97
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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