Triethylamine → 3-(4-t-butylphenyl)-N-[4-(methylsulfonamido)-3-vinylbenzyl]propanamide

HRID 2358414Notes

Reaction equation

HRID 2358414 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH:14]=[CH2:15])[CH:4]=1.C(N(CC)CC)C.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35](O)=[O:36])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(Cl)Cl>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][C:35]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH:14]=[CH2:15])[CH:4]=2)=[O:36])=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 49621733-(4-Tert-butylphenyl)propanoic acidHCID 57665523N-(4-aminomethyl-2-vinylphenyl)methanesulfonamide

Product 1

HCID 118528933-(4-t-butylphenyl)-N-[4-(methylsulfonamido)-3-vinylbenzyl]propanamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[4-(aminomethyl)-2-vinylphenyl]methanesulfonamide (0.23 mol) and was suspended in methylene chloride and treated with triethylamine followed by 3-(4-tert-butyl-phenyl)-propionic acid and DMTMM (40 mg). The resulting mixture was stirred for 2 days at ambient temperature and concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate=3/2) to yield a white solid (73%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was column-chromatographed (hexane/ethylacetate=3/2)

Sources & evidence

ORD record
ord-8565c4098b614421bde48758e68339b3
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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