4-Toluenesulfonyl chloride → tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

HRID 923613Notes

Reaction equation

HRID 923613 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:33]=[CH:32][C:10]([CH2:11][N:12]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:13](=[O:23])[C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[N:3]=1.CC(C)([O-])C.[K+].[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>C1COCC1>[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([NH:1][C:2]2[O:6][N:5]=[C:4]([C:7]3[CH:8]=[CH:9][C:10]([CH2:11][N:12]([CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:13](=[O:23])[C:14]4[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=4)=[CH:32][CH:33]=3)[N:3]=2)(=[O:49])=[O:48])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 71078447tert-butyl 2-(N-(4-(5-amino-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

Product 1

HCID 71112109tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetateYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared using General Procedure 10. To a stirring solution of tert-butyl 2-(N-(4-(5-amino-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-67 (150 mg, 0.331 mmol) in THF (3 mL) was added potassium tert-butoxide (599 μL, 0.992 mmol) at room temperature. After 15 mins a solution of 4-methylbenzene-1-sulfonyl chloride (63.1 mg, 0.331 mmol) in THF (1 mL) was added. After 1 h the reaction mixture quenched with 1 M HCl (30 mL) and then extracted with EA (50 mL). The organic layer was concentrated in vacuo and purified by chromatography (EA/hexanes) to provide 20 mg (10%) of tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-68. LCMS-ESI (m/z) calculated for C29H29N5O8S: 607; found 608 [M+H]+, tR=2.50 min (Method 10).

Workup

  1. customPrepared
  2. customAfter 1 h the reaction mixture quenched with 1 M HCl (30 mL)
  3. extractionextracted with EA (50 mL)
  4. concentrationThe organic layer was concentrated in vacuo
  5. custompurified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-7b34a5645fe7433f9b71af18a0c5702a
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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