Iodine → Limazocic

HRID 2248555Notes

Reaction equation

HRID 2248555 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([CH3:21])([CH2:19][SH:20])[C:10]([NH:12][C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][SH:15])=[O:11].II>C(Cl)Cl>[CH3:8][C:9]1([CH3:21])[CH2:19][S:20][S:15][CH2:14][C@@H:13]([C:16]([OH:18])=[O:17])[NH:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 9859532N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteine

Product 1

HCID 65963LimazocicYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of triethylamine (13.3 g) in methylene chloride (0.5 l), N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteine (15.6 g) dissolved in methylene chloride (0.5 l) and iodine (18.3 g) dissolved in methylene chloride (0.5 l) were added dropwise simultaneously under ice-salt cooling. After the addition, the reaction mixture was stirred for 1 hr at the same temperature. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Separated crystals were collected by filtration to give 8.5 g (55%) of the titled compound.

Workup

  1. additionwere added dropwise simultaneously under ice-salt cooling
  2. additionAfter the addition
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customSeparated crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3079c9fdbba7469baf09558ab8f93498
Source dataset
uspto-grants-1991_08
Patent number
US05041435

Reaction notes

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