1,2-Dichloroethane → HCID 59199861, compound

HRID 84849Notes

Reaction equation

HRID 84849 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:27]C=2C=1.N>CN(C=O)C.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10]([NH2:27])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

Product 1

HCID 59199861HCID 59199861, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of above mentioned (R)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (1.0 g, 4.36 mmol) in DMF (10 ml) was added EDC (1.0 g, 5.24 mmol) and HOBt.H2O (367 mg, 2.4 mmol) at room temperature, 20 min later, it was added ammonia in (7N, 0.6 mL, 4 mmol) at room temperature. After stirring for 30 min, it was diluted with water and EtOAc, organic layer was separated and washed with Sat. NaHCO3, brine, dried and concentrated to give (R)-tert-butyl-1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate (750 mg) as crude oil, which was treated with 4N HCl in Dioxane (5 mL). 30 min later, it was concentrated to give (R)-2-amino-2-cyclopropylacetamide hydrochloride salt.

Workup

  1. customwas separated
  2. washwashed with Sat. NaHCO3, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c92ff849f6fe4bc8816e4a7f5794f884
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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