Hydrochloric Acid → Limazocic

HRID 1090611Notes

Reaction equation

HRID 1090611 reaction equation
BrC(C(OCC)=O)C(OCC)=O.C(N(CC)CC)C.[CH3:20][C:21]([CH3:33])([CH2:31][SH:32])[C:22]([NH:24][C@H:25]([C:28]([OH:30])=[O:29])[CH2:26][SH:27])=[O:23].Cl>C(Cl)Cl>[CH3:20][C:21]1([CH3:33])[CH2:31][S:32][S:27][CH2:26][C@@H:25]([C:28]([OH:30])=[O:29])[NH:24][C:22]1=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69637Diethyl bromomalonateHCID 9859532N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteine

Product 1

HCID 65963LimazocicYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethyl bromomalonate (10.5 g) and triethylamine (8.5 g) in methylene chloride (3.8 l), N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteine (9.5 g) dissolved in methylene chloride (0.3 l) was added dropwise under ice-salt cooling. After the addition, the reaction mixture was stirred for 30 minutes at the same temperature and for 30 minutes at room temperature. The mixture was acidified with 6N hydrochloric acid and washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Separated crystals were collected by filtration to give 6.1 g (65%) of the titled compound.

Workup

  1. additionwas added dropwise under ice-salt cooling
  2. additionAfter the addition
  3. washwashed with saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customSeparated crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-9c16b1bf89a64fd4bd881973e28bbbdd
Source dataset
uspto-grants-1992_01
Patent number
US05082836

Reaction notes

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