1,2-Dichloroethane → HCID 11961339, compound

HRID 1366429Notes

Reaction equation

HRID 1366429 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([NH:16][CH2:17][C:18](O)=[O:19])([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>[O:19]=[C:18]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:17][NH:16][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 31268PyrrolidineHCID 181649HOAt

Product 1

HCID 11961339HCID 11961339, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyrrolidine (248 uL, 3 mmol), N-CBZ-glycine (628 mg, 3 mmol), and HOAt (408 mg, 3 mmol) were dissolved in 10 mL of dichloromethane. NMM (0.66 mL, 6 mmol) was added, followed by EDC (575 mg, 3 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous NaHCO3 solution, and saturated aqueous NH4Cl solution, then dried (Na2SO4) and evaporated to yield phenylmethyl [2-oxo-2-(1-pyrrolidinyl)ethyl]carbamate as a beige solid (782 mg, 100%). LCMS: (M+H)+: 263.1.

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-633f7f47c1234d36a070219b17d47d13
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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