Dimethylformamide → 1-(3-Acetoxy-4-chloro-benzoylamino)-cycloheptanecarboxylic Acid Methyl Ester

HRID 1918299Notes

Reaction equation

HRID 1918299 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=O)(=[O:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[CH3:27][O:28][C:29]([C:31]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:30]>C(Cl)Cl.CC(=O)OCC>[CH3:27][O:28][C:29]([C:31]1([NH:38][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 225700263-Acetoxy-4-chlorobenzoic AcidHCID 42614177Methyl 1-aminocycloheptane-1-carboxylate hydrochloride

Product 1

HCID 671708791-(3-Acetoxy-4-chloro-benzoylamino)-cycloheptanecarboxylic Acid Methyl EsterYield 125.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of step 1 (200 mg, 0.932 mmol) was dissolved in DCM (16 ml), DMF (12 mg) and oxalyl chloride (362 mg, 2.80 mmol) were added and the mixture was stirred at room temperature until completion of the reaction. The volatiles were evaporated in vacuo and the residue dissolved in DCM. The solution was added to a stirred mixture of 1-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (194 mg, 0.932 mmol) in EA/saturated sodium hydrogencarbonate solution with cooling in an ice bath. Stirring continued at room temperature for 2 h. The phases were separated, aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield the title compound (430 mg).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionthe residue dissolved in DCM
  3. temperaturewith cooling in an ice bath
  4. stirringStirring
  5. customThe phases were separated
  6. extractionaqueous phase was extracted with EA
  7. dry with materialthe combined organic phases were dried over sodium sulfate
  8. customevaporated to dryness
  9. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-40a42d875f1943bca82814994477a0a7
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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