1,2-Dichloroethane → HCID 14804457, compound

HRID 1366430Notes

Reaction equation

HRID 1366430 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([NH:16][C@@H:17]([C:19](O)=[O:20])[CH3:18])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>ClCCl.CCOC(C)=O>[CH3:18][C@@H:17]([NH:16][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:19](=[O:20])[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 70832N-Cbz-d-alanineHCID 181649HOAt

Product 1

HCID 14804457HCID 14804457, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (1668 uL, 2 mmol), N-CBZ-D-alanine (446 mg, 2 mmol), and HOAt (272 mg, 2 mmol) were dissolved in 6 mL of dichloromethane. NMM (0.44 mL, 4 mmol) was added, followed by EDC (382 mg, 2 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with EtOAc, washed with water, saturated aqueous NaHCO3 solution, and saturated aqueous NH4Cl solution, then dried (Na2SO4) and evaporated to yield phenylmethyl [(1R)-1-methyl-2-oxo-2-(1-pyrrolidinyl)ethyl]carbamate as a white solid (496 mg, 90%). LCMS: (M+H)+: 277.2.

Workup

  1. washwashed with water, saturated aqueous NaHCO3 solution, and saturated aqueous NH4Cl solution
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-806a7f022a6349489e1eaab18d3cd1fd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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