Iodine → 1053178-96-3

HRID 1027569Notes

Reaction equation

HRID 1027569 reaction equation
C([S:4][CH2:5][CH:6]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][S:8]C(=O)C)(=O)C.[OH-].[Na+].II>C(O)C.ClCCl>[C:16]([O:15][C:13](=[O:14])[NH:12][CH:6]1[CH2:7][S:8][S:4][CH2:5]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 545671HCID 545671, compound

Product 1

HCID 545949731053178-96-3Yield 71.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of thioacetic acid S-(3-acetylsulfanyl-2-tert-butoxycarbonylamino-propyl) ester (330 mg) in ethanol (5 ml) was treated with 2.5 ml of 1N sodium hydroxide for 1 hour at room temperature. The yellow solid turned green-brown. The reaction mixture was diluted with dichloromethane (25 ml) and then an aqueous solution of 0.1M iodine (10 ml) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour and quenched by addition of 1M sodium bisulfite solution. The organic layer was separated, washed with water, dried over sodium sulfate and the solvent evaporated in vacuo to afford the title product (170 mg). 1H-NMR (CDCl3, 400 MHz): 5.00 (br s, 1H), 4.90 (m, 1H), 3.15 (d, 2H), 3.05 (d, 2H), 1.40 (s, 9H).

Workup

  1. customquenched by addition of 1M sodium bisulfite solution
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e40ab3fc2c2b447f9dd012af56b3ded3
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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