1,2-Dichloroethane → (R)-tert-butyl 2-amino-1-cyclopropyl-2-oxoethylcarbamate

HRID 84847Notes

Reaction equation

HRID 84847 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:26]C=2C=1.N.CO>CN(C=O)C.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10]([NH2:26])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 887MethanolHCID 757711-HydroxybenzotriazoleHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid

Product 1

HCID 67776181(R)-tert-butyl 2-amino-1-cyclopropyl-2-oxoethylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-2-(tert-butoxycarbonylamino)-2-cyclopropylacetic acid (430 mg, 2 mmol) in DMF (6 ml) was added EDC (461 mg, 2.4 mmol) and HOBt. H2O (367 mg, 2.4 mmol) at room temperature, 20 min later, it was added ammonia in MeOH (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-2-amino-1-cyclopropyl-2-oxoethylcarbamate (330 mg) as crude oil, which was treated with 4N HCl in Dioxane (2 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-4bb620dcfda446d39180ec362c5c3cac
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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