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

HRID 2201078
Notes
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Reaction equation

HRID 2201078 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-1e98d85c885942508cc428bcb6b63cdb
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359375B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes