1,2-Dichloroethane → HCID 59199861, compound

HRID 2201080Notes

Reaction equation

HRID 2201080 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.CO>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

9

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 887MethanolHCID 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 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-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-2416f999230e4d3f87b6f3371efd7a89
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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