2,6-Dimethoxybenzoyl chloride → HCID 118308159, compound

HRID 1750464

Reaction equation

HRID 1750464 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:20])[C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19].N[C@H]1CCC[C@@H]1NC(=O)OC(C)(C)C.COC1C=CC=C(OC)C=1C([Cl:41])=O>>[ClH:41].[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:20])[C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19]

Participants

4

Reactant 3

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 118308327HCID 118308327, compound2×

Product 1

HCID 118308159HCID 118308159, compound

Procedure

Prepared according to the procedure for N-[(1S,2R)-2-aminocyclopentyl]-2,6-dimethoxybenzamide hydrochloride (Intermediate 3) from tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 1.0 g, 4.99 mmol) and 2,6-dimethoxybenzoyl chloride (CAS number 1989-53-3; 1.50 g, 7.99 mmol) except that after the reaction was complete it was partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic frit and concentrated in vacuo. The Boc protected intermediate was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to give a white solid. After deprotection with HCl in 1,4-dioxane, azeotropic distillation from toluene afforded the title compound.

Workup

  1. customPrepared
  2. customwas partitioned between DCM
  3. filtrationa saturated solution of sodium bicarbonate, filtered through a hydrophobic frit
  4. concentrationconcentrated in vacuo
  5. customThe Boc protected intermediate was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  6. customto give a white solid
  7. distillationAfter deprotection with HCl in 1,4-dioxane, azeotropic distillation from toluene

Sources & evidence

ORD record
ord-f54d203a12cf4e0da23faa0ddabeaa9d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Linked notes

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