1,2-Dichloroethane → HCID 69148098, compound

HRID 2114849Notes

Reaction equation

HRID 2114849 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:16][CH:17]([NH:19][CH3:20])[CH3:18])[CH2:12][C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:18][CH:17]1[N:19]([CH3:20])[C:13](=[O:14])[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16]1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 69148003HCID 69148003, compound

Product 1

HCID 69148098HCID 69148098, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[(benzyloxy)carbonyl]-N-[2-(methylamino)propyl]glycine (2.42 g, 8.63 mmol) in DMF (40 mL) was treated with EDC (1.66 g, 8.63 mmol) and stirred at room temperature overnight. The reaction was diluted with EtOAc and washed once each with aqueous 1N HCl, saturated aqueous NaHCO3, and brine. The combined aqueous layers were extracted once with EtOAc, and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was subjected to column chromatography eluting with a gradient of 50-100% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product.

Workup

  1. washwashed once each with aqueous 1N HCl, saturated aqueous NaHCO3, and brine
  2. extractionThe combined aqueous layers were extracted once with EtOAc
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluting with a gradient of 50-100% EtOAc/hexanes
  7. customCollection and concentration of the appropriate fractions
  8. customafforded the product

Sources & evidence

ORD record
ord-6ced13139d6f49f687a0bb61976f750e
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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