Methyl iodide → HCID 54435265, compound

HRID 892803Notes

Reaction equation

HRID 892803 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]([C:19]1[CH:20]=[C:21]([NH:25][C:26]([CH:28]2[CH2:32][S:31][CH:30]([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[N:29]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:27])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.[C:48](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[C:11]([C:19]1[CH:20]=[C:21]([N:25]([CH3:48])[C:26]([CH:28]2[CH2:32][S:31][CH:30]([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[N:29]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:27])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 19894104N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide

Product 1

HCID 54435265HCID 54435265, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium hexamethyl disilazide (0.6 mL, 1.0M in hexanes) was added at 0° C. under nitrogen to a solution of N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide prepared as described in example 2 (202 mg, 0.41 mmol), in dry THF (4 mL, 0.1 mL). The mixture was stirred for 20 min then methyl iodide (25 μL) was added and the mixture stirred for an additional 8 hours. The reaction mixture was partioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfated and the solvent removed in vacuo. The residue was purified by flash chromatography eluting with hexanes:ethyl acetate (12:3) to yield the desired product (0.53 g, 45%).

Workup

  1. customprepared
  2. stirringthe mixture stirred for an additional 8 hours
  3. dry with materialThe organic phase was dried over magnesium
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexanes:ethyl acetate (12:3)

Sources & evidence

ORD record
ord-df05131f53e94f029915beb275c8bdc1
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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