1,2-Dichloroethane → HCID 58009747, compound

HRID 2114830Notes

Reaction equation

HRID 2114830 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].[C:9]([NH:19][CH2:20][C:21]([OH:23])=O)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:12]([O:11][C:9]([NH:19][CH2:20][C:21]([N:5]([CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])[CH3:6])=[O:23])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 85032,2-DimethoxyethylmethylamineHCID 14349BenzyloxycarbonylglycineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 58009747HCID 58009747, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2,2-dimethoxyethyl)-N-methylamine (760 g, 6.38 mmol), N-CBZ-glycine (1337.6 g, 6.39 mol), EDC (1225.8 g, 6.39 mol), and HOBt (107.7 g, 0.70 mol), and N,N-diisopropylethylamine (172 mL) in anhydrous DMF (12 L) was stirred at room temperature overnight. The reaction mixture was diluted with water (24 L) and extracted with dichloromethane (3×10 L). The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound.

Workup

  1. extractionextracted with dichloromethane (3×10 L)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4750d92cee24d5c85a28677a0706ec3
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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