1,2-Dichloroethane → 1-(4-Acetyl-3-hydroxy-benzoylamino)-cycloheptanecarboxylic Acid Methyl Ester

HRID 1475705Notes

Reaction equation

HRID 1475705 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C1C=CC2N(O)N=NC=2C=1.[C:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][C:28]=1[OH:36])(=[O:26])[CH3:25].C(Cl)CCl>CN(C=O)C>[CH3:2][O:3][C:4]([C:6]1([NH:13][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([C:24](=[O:26])[CH3:25])=[C:28]([OH:36])[CH:29]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 106549474-acetyl-3-hydroxybenzoic acidHCID 42614177Methyl 1-aminocycloheptane-1-carboxylate hydrochloride

Product 1

HCID 671697031-(4-Acetyl-3-hydroxy-benzoylamino)-cycloheptanecarboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Amino-cycloheptanecarboxylic acid methyl ester hydrochloride (968 mg, 4.66 mmol), HOBT (105 mg, 0.78 mmol) and 4-acetyl-3-hydroxy-benzoic acid (700 mg, 3.89 mmol) were dissolved in DMF (5 ml). EDIA (3.01 g, 23.3 mmol) and EDC were added and the mixture was stirred at room temperature for 72 h. Then the mixture was partitioned between EA and saturated sodium chloride solution, the aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield the title compound.

Workup

  1. customThen the mixture was partitioned between EA and saturated sodium chloride solution
  2. extractionthe aqueous phase was extracted with EA
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-114d7d1a6ad34d3f8dd00dcfd8429677
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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