Lithium iodide → HCID 22645076, compound

HRID 1976483Notes

Reaction equation

HRID 1976483 reaction equation
C[O:2][C:3]([CH:5]1[C:10]([CH3:12])([CH3:11])[S:9][CH2:8][CH2:7][N:6]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:4].[I-].[Li+]>C(OCC)(=O)C>[C:33]([O:32][C:30]([NH:29][CH2:28][CH2:27][CH2:26][C:25]#[C:24][CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:6]2[CH2:7][CH2:8][S:9][C:10]([CH3:12])([CH3:11])[CH:5]2[C:3]([OH:4])=[O:2])(=[O:15])=[O:14])=[CH:17][CH:18]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 22644979HCID 22644979, compound

Product 1

HCID 22645076HCID 22645076, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.764 g (1.41 mmol) of methyl4-{[4-({6-[(tert-butoxycarbonyl)amino]-2-hexynyl}oxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholinecarboxylate and 3.77 g (28.2 mmol) of lithium iodide in 30 mL of ethyl acetate was heated to reflux for 18h. The resulting reaction was acidified, washed with water, an aqueous solution of Na2S2O3 , brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 0.5% methanol/dichloromethane to provide 0.417 g (56%) of 4-{[4-({6-[(tert-butoxycarbonyl)amino]-2-hexynyl}oxy)phenyl]sulfonyl}-2,2-dimethyl-3-thiomorpholine carboxylic acid as a white solid. Electrospray Mass Spec: 527.2(M+H)+

Workup

  1. temperatureto reflux for 18h
  2. customThe resulting reaction
  3. washwashed with water
  4. dry with materialan aqueous solution of Na2S2O3 , brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 0.5% methanol/dichloromethane

Sources & evidence

ORD record
ord-e5ce5e3471034b44803c27dbd1b5170f
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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