Acetyl chloride → HCID 178471808, compound

HRID 420774Notes

Reaction equation

HRID 420774 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)[CH3:3].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:22](=[O:24])[CH3:23])[CH2:11][CH2:12]1)[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178471807HCID 178471807, compound

Product 1

HCID 178471808HCID 178471808, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (1.0 g, 4.51 mmol) (Example A, step 2) was dissolved in dichloromethane and triethylamine (1.89 ml, 13.5 mmol) was added. Acetyl chloride (0.35 ml, 4.96 mmol) was added drop wise and the reaction mixture stirred for 5 hours at room temperature. The reaction mixture was quenched with saturated NaHCO3-solution and extracted with dichloromethane. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product (804 mg, 78%) [MS: m/e=228.3/229.3 (M+H+)] was obtained as a white solid and used without any further purification for the next step.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3-solution
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c71d3e37f532465d96b64caa05cb7fb5
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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