Dichloromethane → HCID 20661970, compound

HRID 2082217Notes

Reaction equation

HRID 2082217 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[CH3:25]CN=C=NCCCN(C)C.[ClH:36].[CH2:37]([Cl:39])[Cl:38]>CN(C)C1C=CN=CC=1>[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:25][C:37]([Cl:39])([Cl:38])[Cl:36]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1537081-(Phenylmethyl) hydrogen N-((1,1-dimethylethoxy)carbonyl)-L-glutamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 20661970HCID 20661970, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of Boc-Glu-OBzl (1.00 g) and TceOH (0.53 g) in methylene chloride (15 ml) were added 4-dimethylaminopyridine (0.04 g) and WSC.HCl (0.57 g) successively under ice cooling. The mixture was stirred for 3 hours at the same temperature. After evaporation, the residue was extracted with ethyl acetate. The organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate solution, water and saturated sodium chloride solution, and dried over magnesium sulfate. The evaporated residue was crystallized with petroleum ether, filtered and dried to give Boc-Glu(OTce)-OBzl (1.01 g).

Workup

  1. customAfter evaporation
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate solution, water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe evaporated residue was crystallized with petroleum ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-c1520dcacdc8495bb7b50bfcd1693a5b
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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