1,2-Dichloroethane → HCID 57889129, compound

HRID 1820216Notes

Reaction equation

HRID 1820216 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([C:11]([OH:13])=O)[CH2:6]1)=[O:4].C1C=CC2N(O)N=[N:20][C:18]=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[CH3:18][NH:20][C:11]([CH:7]1[CH2:8][CH2:9][CH2:10][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)=[O:13]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11194755AG-G-90137

Product 1

HCID 57889129HCID 57889129, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-cis-3-(Methoxycarbonyl)cyclohexanecarboxylic acid (500 mg, 2.69 mmol), methylamine, HCl (218 mg, 3.22 mmol), HOBT (493 mg, 3.22 mmol), EDC (618 mg, 3.22 mmol) and triethylamine (0.75 mL, 5.37 mmol) were mixed and stirred in methylene chloride (10 mL) at 25° C. The reaction was stirred overnight then washed with 1N HCl, sat'd sodium bicarbonate, and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give (±)-cis-3-(methyl 3-(methylcarbamoyl)cyclohexanecarboxylate (460 mg, 2.309 mmol, 86% yield) as a white glass. MS found: (M+H)+=200.10.

Workup

  1. washthen washed with 1N HCl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6139323a471848579bb113b952bab6c3
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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