Diethyl squarate → HCID 54525291, compound

HRID 1289910Notes

Reaction equation

HRID 1289910 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[NH2:13][C@@H:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:15]>C(O)C>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[NH:13][C@H:14]([CH3:15])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:10]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 5324845(R)-3,3-Dimethyl-2-aminobutane2×

Product 1

HCID 54525291HCID 54525291, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (10 g, 59 mmol) and (R)-2-amino-3,3-dimethylbutane (353 mL of a 0.2M solution in absolute ethanol, 71 mmol) was stirred at room temperature for 24 hours. Another portion of (R)-2-amino-3,3-dimethylbutane (150 mL of a 0.2M solution in absolute ethanol, 30 mmol) was added, and the resulting solution was stirred at room temperature for 24 hours. The slurry was filtered, and the filtrate concentrated under reduced pressure. The resulting solid was triturated with hexane:ethyl acetate (150:5 mL), and washed with hexane to give 9.78 g (74%) of a white solid: 1H NMR: (DMSO-d6): δ 8.72 and 8.50 (two d, 1H, rotamers), 4.65 (m, 2H), 3.90 and 3.42 (two m, H, rotamers), 1.37 and 1.35 (two overlapping t, 2H, rotamers), 1.10 (two overlapping d, 3H, rotamers), 0.85 and 0.84 (two s, 9H, rotamers) ppm. IR(KBr): 3150, 2950, 1800, 1700 cm-1 ; MS (m/z): 225 (M+); Anal. Calcd. for C12H19NO3 : C, 63.98; H, 8.50; N, 6.22. Found: C, 64.33; H, 8.54; N, 6.52.

Workup

  1. filtrationThe slurry was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe resulting solid was triturated with hexane
  4. washethyl acetate (150:5 mL), and washed with hexane

Sources & evidence

ORD record
ord-444c3dd72dbf415ea9d179feb110c106
Source dataset
uspto-grants-1998_05
Patent number
US05750574

Reaction notes

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