Water → HCID 13535921, compound

HRID 365068Notes

Reaction equation

HRID 365068 reaction equation
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1.O>C1COCC1>[C:3]([C:2]([NH:1][C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=1)=[O:24])([CH3:9])[CH:6]([CH3:8])[CH3:7])(=[O:4])[NH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 97937732-Amino-2,3-dimethylbutanamide

Product 1

HCID 13535921HCID 13535921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture containing 13.0 g (0.10 mol) of 2-amino-2,3-dimethylbutyramide and 15.3 mL (0.11 mol) of triethylamine in 150 mL of dry THF is treated dropwise at 5° to 10° C. with a solution of 15.5 g (0.10 mol) of p-toluoyl chloride in 25 mL dry THF. After being allowed to warm to ambient temperatures over a 16 hour period, the reaction mixture is treated with 50 mL water and stirred for one hour. The resulting three phases are filtered; the filtrate is separated and the aqueous phase is extracted with 150 mL ethyl acetate. All organic phases are combined, washed with 100 mL of a saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. A white solid residue is obtained which weighs 17.3 g, mp 145°-152° C. The nmr spectrum is consistent with the desired structure.

Workup

  1. temperatureto warm to ambient temperatures over a 16 hour period
  2. filtrationThe resulting three phases are filtered
  3. customthe filtrate is separated
  4. extractionthe aqueous phase is extracted with 150 mL ethyl acetate
  5. washwashed with 100 mL of a saturated NaCl solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customA white solid residue is obtained which

Sources & evidence

ORD record
ord-cbee0a3c45404b25a95995366e415487
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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