1,2-Dichloroethane → (R)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamate

HRID 332799Notes

Reaction equation

HRID 332799 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])[CH3:3].C1C=C2[N:25]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:25][C:16](=[O:18])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:4])([CH3:3])[CH3:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10944841(R)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamateYield 89.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Boc-D-phenylglycine (500 mg, 1.99 mmol), HOBt hydrate (370 mg, 2.41 mmol) and EDC (500 mg, 2.60 mmol) in DMF (8 mL) was stirred at room temperature for 30 min. Conc. NH4OH (1.00 mL) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamate as a solid (446 mg).

Workup

  1. customOrganic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ad1f4d32f7e4a7d9ee3ee1fba42625b
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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