4-Tert-butylcinnamic acid → 3-(4-t-Butyl-phenyl)-N-(3-methyl-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2423336Notes

Reaction equation

HRID 2423336 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>O1CCCC1>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([CH:26]=[CH:27][C:28]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:3]([CH3:2])[CH:4]=2)=[O:29])=[CH:24][CH:25]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 7248384-Tert-butylcinnamic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21097529N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride

Product 1

HCID 672443073-(4-t-Butyl-phenyl)-N-(3-methyl-4-methanesulfonylamino-benzyl)-acrylamideYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-4-methanesulfonylaminobenzylamine hydrochloride (140 mg, 0.56 mmol), 3-(4-t-butylphenyl)acrylic acid (1.1 eq, 0.13 g), and DMTMM (1.1 eq, 0.185 g) were added into 25 ml tetrahydrofuran. The reaction mixture was stirred 12 hours at room temperature. After confirming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, washed 1N HCl solution. And the combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=2/1) to yield a solid (49 mg).

Workup

  1. customthe completion of the reaction with TLC
  2. extractionthe reaction mixture was extracted with ethylacetate
  3. washwashed 1N HCl solution
  4. dry with materialAnd the combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-561380ea9a794275bf2e92a23cd9d6f6
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

Loading…