(R)-3,3-Dimethyl-2-aminobutane → (R)-3-(2-hydroxy-6-methylphenylamino)-4-(2,2,1-trimethylpropyl-amino)-cyclobut-3-ene-1,2-dione

HRID 357297Notes

Reaction equation

HRID 357297 reaction equation
C(O[C:4]1[C:5](=[O:18])[C:6](=[O:17])[C:7]=1[NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:16])C.[NH2:19][C@@H:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:21]>C(O)C.ClCCl>[OH:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:9]=1[NH:8][C:7]1[C:6](=[O:17])[C:5](=[O:18])[C:4]=1[NH:19][C@H:20]([CH3:21])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 5324845(R)-3,3-Dimethyl-2-aminobutaneHCID 189374263-Ethoxy-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 54402716(R)-3-(2-hydroxy-6-methylphenylamino)-4-(2,2,1-trimethylpropyl-amino)-cyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Ethoxy-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione (0.4 g, 1.62 mmol) and (R)-2-amino-3,3-dimethylbutane (16 mL of a 0.2M solution in absolute ethanol, 3.20 mmol) in dichloromethane (4 mL) was heated at 80° C. for 4 hours. The reaction mixture was cooled, concentrated under reduced pressure, and the resulting residue was trituated with hexane:ethyl acetate (1:1) to produce a solid, which was filtered and rinsed with hexane:ethyl acetate (1:1). Chromatography with 10% methanol in dichloromethane gave (R)-3-(2-hydroxy-6-methylphenylamino)-4-(2,2,1-trimethylpropyl-amino)-cyclobut-3-ene-1,2-dione, 0.24 g (0.79 mmol, 49%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customto produce a solid, which
  4. filtrationwas filtered
  5. washrinsed with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-428e3828cce542bcb5e4bd46b7fb5729
Source dataset
uspto-grants-1998_11
Patent number
US05840764

Reaction notes

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