1,2-Dichloroethane → HCID 70212244, compound

HRID 2269344Notes

Reaction equation

HRID 2269344 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH:21]1[CH:22]=C[C:24]2[N:29](O)N=[N:27][C:25]=2[CH:26]=1.NC1C=NC=CC=1>CN(C=O)C>[N:29]1[CH:22]=[CH:21][CH:26]=[C:25]([NH:27][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:24]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 70212244HCID 70212244, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid (3 g, 12.99 mmol) in DMF (25 mL) is added EDC (2.73 g, 14.29 mmol) and HOBT (1.93 g, 14.29 mmol). The resulting solution is stirred at 25° C. for 0.5 h and 3-aminopyridine (1.83 g, 19.48 mmol) is; added and the reaction is heated to 50° C. for 18 h. The mixture is concentrated, diluted with EtOAc (50 mL), and washed with saturated aqueous sodium bicarbonate. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to provide (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid 3-pyridylamide as a foam (1.6 g, 40% yield).

Workup

  1. additionadded
  2. temperaturethe reaction is heated to 50° C. for 18 h
  3. concentrationThe mixture is concentrated
  4. additiondiluted with EtOAc (50 mL)
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e5be89cef134691b433808039ee3d46
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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