Hydrochloric Acid → N-acetyl-4-mesyloxy-L-proline ethyl ester

HRID 1723900Notes

Reaction equation

HRID 1723900 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][C:9](=[O:19])[C@@H:10]1[CH2:14][CH:13]([OH:15])[CH2:12][N:11]1[C:16](=[O:18])[CH3:17])[CH3:7].C(N(CC)CC)C.Cl>C(Cl)(Cl)Cl>[CH2:6]([O:8][C:9](=[O:19])[C@@H:10]1[CH2:14][CH:13]([O:15][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][N:11]1[C:16](=[O:18])[CH3:17])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22794895N-acetyl-4-hydroxy-L-proline ethyl ester

Product 1

HCID 86601300N-acetyl-4-mesyloxy-L-proline ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

457 g of methanesulfonyl chloride was added dropwise to a solution of 1020 g of N-acetyl-4-hydroxy-L-proline ethyl ester, 435 g of triethylamine and 1.9 L of chloroform at not higher than 15° C. while cooling. After stirring for 30 minutes, 1N hydrochloric acid (0.6 L) was added, and the layers were separated. The organic layer was washed with 5% aqueous sodium bicarbonate (600 g), washed with water (0.6 L), dried over magnesium sulfate, and concentrated under reduced pressure to obtain 802 g of N-acetyl-4-mesyloxy-L-proline ethyl ester as an oil.

Workup

  1. temperaturewhile cooling
  2. customthe layers were separated
  3. washThe organic layer was washed with 5% aqueous sodium bicarbonate (600 g)
  4. washwashed with water (0.6 L)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8006c59322da438d8c0045fcaa32c7c4
Source dataset
uspto-grants-2009_02
Patent number
US07485665B2

Reaction notes

Loading…