Diisopropylethylamine → HCID 68897131, compound

HRID 897275Notes

Reaction equation

HRID 897275 reaction equation
Cl[C:2]([C:4]1[C:5]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:3].Cl.C[O:18][C:19](=[O:22])[CH2:20][NH2:21].[CH:23](N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:23][N:21]([C:2]([C:4]1[C:5]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:3])[CH2:20][C:19]([OH:18])=[O:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 22346344HCID 22346344, compound

Product 1

HCID 68897131HCID 68897131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of isopropyl 3-(chlorocarbonyl)pyridine-2-carboxylate (prepared as in P. Ornstein et. al. J. Med. Chem. 1989, 32, 827) (6.577 g, 31.44 mmol) in CH2Cl2 (50 ml) was added dropwise to a solution of glycine methyl ester hydrochloride (4.34 g, 34.58 mmol) and diisopropylethylamine (12.6 ml, 72.31 mmol) in CH2Cl2 (65 ml) at 0 C. The reaction was stirred for 16 hrs during which time the ice bath was allowed to expire. The solvent was evaporated in vacuo and the residue was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-623e713fb5cf4b0f9f45bda318ee280a
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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