Methanesulfonyl chloride → HCID 56592714, compound

HRID 2359273Notes

Reaction equation

HRID 2359273 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[S:31](Cl)([CH3:34])(=[O:33])=[O:32]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:12][S:31]([CH3:34])(=[O:33])=[O:32])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 58046306HCID 58046306, compound

Product 1

HCID 56592714HCID 56592714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3,4-dichlorobenzyl)-3-methoxybenzamide (Preparation 155, 155 mg, 0.50 mmol) in anyhydrous THF (5 mL) was added 1M LiHMDS (1.25 mL, 1.25 mmol) via syringe. The mixture was stirred for 20 minutes before adding mesyl chloride (0.116 mL, 1.50 mmol) and then stirred for 18 hours at room temperature. The reaction was quenched with the addition of 2M HCl (20 mL), and the aqueous was extracted with EtOAc (3×20 mL). The combined organics were concentrated in vacuo and the residue was purified by silica gel column chromatography eluting with a gradient of 25% EtOAc in heptane to 100% EtOAc. The title compound was obtained as a white solid (40 mg, 21%).

Workup

  1. stirringstirred for 18 hours at room temperature
  2. customThe reaction was quenched with the addition of 2M HCl (20 mL)
  3. extractionthe aqueous was extracted with EtOAc (3×20 mL)
  4. concentrationThe combined organics were concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with a gradient of 25% EtOAc in heptane to 100% EtOAc

Sources & evidence

ORD record
ord-ca2bb36889ba49ee987d5d94f2afe278
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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