3-Chlorobenzoic Acid → Methyl 3-[(3-chlorobenzoyl)amino]adamantane-1-carboxylate

HRID 1503259Notes

Reaction equation

HRID 1503259 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([NH2:16])([CH2:9]3)[CH2:7]1)[CH2:13]2)=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([NH:16][C:8]12[CH2:14][CH:12]3[CH2:11][CH:10]([CH2:15][C:6]([C:4]([O:3][CH3:2])=[O:5])([CH2:13]3)[CH2:7]1)[CH2:9]2)=[O:22]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 2852886Methyl 3-aminoadamantane-1-carboxylate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 117702477Methyl 3-[(3-chlorobenzoyl)amino]adamantane-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-adamantane-1-carboxylic acid methyl ester HCl salt (Hermogenes N. J. et al.; U.S. Pat. No. 7,947,680 B2) (160 mg, 0.65 mmol) and 3-chlorobenzoic acid (130 mg, 0.78 mmol) in DMF (5 mL) was added DIEA (340 mg, 2.6 mmol) and HATU (300 mg, 0.78 mmol) under N2. After stirring at room temperature for an hour, the reaction was quenched with brine, the aqueous layer was extracted with ethyl acetate (3×20 mL), and the combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1) to afford 220 mg (97%) of the title compound, methyl 3[(3-chlorobenzoyl)amino]adamantane-1-carboxylate, as a white solid. ESI-MS m/z: 348 (M+H)+.

Workup

  1. customthe reaction was quenched with brine
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-83540860e4dc4ac4a888fddb379bc55c
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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