1,2-Dichloroethane → HCID 22135199, compound

HRID 1178314Notes

Reaction equation

HRID 1178314 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:10]([OH:12])=O)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:27][CH:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>C(Cl)Cl.CN(C=O)C.O>[CH3:27][CH:28]([CH3:32])[CH2:29][CH2:30][NH:31][C:10]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:12]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7894IsoamylamineHCID 757711-HydroxybenzotriazoleHCID 18317887HCID 18317887, compound

Product 1

HCID 22135199HCID 22135199, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To 1-(methoxycarbonyl)cyclopentanecarboxylic acid (630 mg, 3.7 mmol) in CH2Cl2/DMF (5:1, 37 mL) at 0° C. was added HOBT (730 mg, 4.8 mmol) and EDC (920 mg, 4.8 mmol). The mixture was stirred for 10 min then 3-methylbutylamine (640 mg, 7.4 mmol) was added and stirring was continued for 1 h. The solution was poured into water and the layers separated. The aqueous layer was extracted with methylene chloride and the combined extracts were washed with water, 1N HCl, sat'd NaHCO3, dried over magnesium sulfate, and concentrated to a glassy solid (800 mg, 90%). MS [M+H]+ 243.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. washthe combined extracts were washed with water, 1N HCl
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a glassy solid (800 mg, 90%)

Sources & evidence

ORD record
ord-5d53c98907664b8a84b3fd431ac87a5c
Source dataset
uspto-grants-2007_10
Patent number
US07276496B2

Reaction notes

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