(R)-camphorsulfonic acid → tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate.(1R)-10-camphorsulfonate

HRID 1063898Notes

Reaction equation

HRID 1063898 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@@:24]12([CH2:34][S:35]([OH:38])(=[O:37])=[O:36])[C:31]([CH3:33])([CH3:32])[CH:28]([CH2:29][CH2:30]1)[CH2:27][C:25]2=[O:26]>C(O)C>[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@@:24]12([CH2:34][S:35]([O-:38])(=[O:36])=[O:37])[C:31]([CH3:33])([CH3:32])[CH:28]([CH2:29][CH2:30]1)[CH2:27][C:25]2=[O:26]

Participants

4

Reactant 2

HCID 131278(R)-camphorsulfonic acidHCID 22276399HCID 22276399, compound

Product 1

HCID 86588733tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate.(1R)-10-camphorsulfonateYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-[7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (3.03 g) in ethanol (90 ml) was added (1R)-10-camphorsulfonic acid (912 mg) at 80° C. The clear solution was allowed to cool to room temperature with stirring for 2 hours to form crystalline solids. After being cooled on an ice bath for 30 minutes, the solids were collected and washed with ethanol to give tert-butyl 2-[(S)-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate•(1R)-10-camphorsulfonate (1.79 g, 91.6% ee) as a white solid.

Workup

  1. customto form crystalline solids
  2. temperatureAfter being cooled on an ice bath for 30 minutes
  3. customthe solids were collected
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-d87751580058451885e59b40ab9dd024
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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