1,2-Dichloroethane → HCID 86730098, compound

HRID 873492Notes

Reaction equation

HRID 873492 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([N:21]([CH2:22][CH3:23])[C:16]([CH:13]1[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1)=[O:18])[CH3:20]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acid

Product 1

HCID 86730098HCID 86730098, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, 1-[(benzyloxy)carbonyl]-3-pyrrolidinecarboxylic acid (500 mg) was dissolved in DMF (5 mL), added with N,N-diethylamine (0.293 g), further with EDC (769 mg) and HOBt (542 mg) and stirred at room temperature for 72 hours. The reaction solution was diluted with ethyl acetate, sequentially washed with 1 N hydrochloric acid, a 1 N sodium hydroxide aqueous solution, water and a saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=95:5→0:1) to give the titled compound (556 mg) having the following physical properties.

Workup

  1. washsequentially washed with 1 N hydrochloric acid
  2. dry with materiala 1 N sodium hydroxide aqueous solution, water and a saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent
  3. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=95:5→0:1)

Sources & evidence

ORD record
ord-faa630fda3354187a42b14669b9fb258
Source dataset
uspto-grants-2015_03
Patent number
US08975409B2

Reaction notes

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