Lithium iodide → HCID 22645076, compound

HRID 2084952Notes

Reaction equation

HRID 2084952 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 methyl-4-{[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 18 h. 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 18 h
  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-7a993567c791443385f0b22a6b01c6df
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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