Water → HCID 58331114, compound

HRID 625827Notes

Reaction equation

HRID 625827 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.S(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].O.[Br:42][CH2:43][CH2:44]Br>ClCCl>[Br:42][CH2:43][CH2:44][O:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 9836914Tetrabutylammonium hydrogen sulphiteHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 58331114HCID 58331114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.98 g (4 mmol) of 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dioate (ALDRICH) was dissolved in 36 ml of 1,2-dibromoethane and cooled in an ice-bath. After addition of 1.36 g (4 mmol) of tetrabutylammonium bisulphite, 18 ml of 50% strength aqueous sodium hydroxide solution are added, and the mixture is stirred on ice for 2 hours and at room temperature overnight. After addition of 200 ml of water and 200 ml of dichloro-methane, the organic phase was washed once more with water, dried over sodium sulphate and filtered, and the filtrate was concentrated. The resulting crude product is chromatographed on silica gel using a dichloromethane/ethyl acetate gradient, and the appropriate fractions are combined and concentrated. Yield: 60 mg (4.3%)

Workup

  1. temperaturecooled in an ice-bath
  2. additionare added
  3. washthe organic phase was washed once more with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe resulting crude product is chromatographed on silica gel using a dichloromethane/ethyl acetate gradient
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-414adeb22e7e4c5598dc66504beefff1
Source dataset
uspto-grants-2016_04
Patent number
US09308282B2

Reaction notes

Loading…