Sodium Carbonate → tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-4-dimethylaminosulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate

HRID 1063911Notes

Reaction equation

HRID 1063911 reaction equation
[Br:1][C:2]1[S:6][C:5]([C@:7]2([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:13](=[O:15])(=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C@@]12(CS([O-])(=O)=O)C(C)(C)C(CC1)CC2=O.[CH3:39][N:40]([CH3:45])[S:41](Cl)(=[O:43])=[O:42].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Br:1][C:2]1[S:6][C:5]([C@:7]2([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:13](=[O:15])(=[O:14])[CH2:12][CH2:11][N:10]([S:41]([N:40]([CH3:45])[CH3:39])(=[O:43])=[O:42])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 83372Dimethylsulphamoyl chlorideHCID 86588733tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate.(1R)-10-camphorsulfonate

Product 1

HCID 69747177tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-4-dimethylaminosulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetateYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate•(1R)-10 -camphorsulfonate (2.00 g), dimethylaminosulfonyl chloride (569 mg) and 2M aqueous sodium carbonate (10.6 ml) in dioxane (40 ml) was stirred for 2.5 days at room temperature. After the reaction solution was concentrated in vacuo, the mixture was diluted with water. The obtained suspension was stirred for 30 minutes under ice-cooling. The resulting solid was collected, washed with water and dried in vacuo to give tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-4-dimethylaminosulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (1.449 g) as a white solid.

Workup

  1. concentrationAfter the reaction solution was concentrated in vacuo
  2. additionthe mixture was diluted with water
  3. stirringThe obtained suspension was stirred for 30 minutes under ice-
  4. temperaturecooling
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bf49647407f74335a0dc220ede2f55a1
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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