2-Methylbenzoyl chloride → HCID 53747028, compound

HRID 1018329Notes

Reaction equation

HRID 1018329 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:22])[CH:6]([NH2:21])[C:7](=[O:20])[CH2:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)[CH3:3].[CH3:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>CN(C=O)C.C1COCC1>[CH2:2]([O:4][C:5](=[O:22])[CH:6]([NH:21][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[CH3:23])[C:7](=[O:20])[CH2:8][CH2:9][C:10]12[CH2:17][CH:16]3[CH2:18][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:19]1)[CH2:11]2)[CH3:3]

Participants

5

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 69686519HCID 69686519, compound

Product 1

HCID 53747028HCID 53747028, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

5-Adamantan-1-yl-2-amino-3-oxo-pentanoic acid ethyl ester hydrochloride (prepared using the method of T. W. von Geldem & C. Hutchins et al, J. Med. Chem. 1996, 39, 957) (3.30 g, 10.0 mmol) was suspended in DMF (15 ml) and a solution of 2-methylbenzoyl chloride (1.55 g 10.0 mmol) in THF (15 ml) was added. The mixture was stirred at room temperature and a solution of N,N-diispropylethylamine (3.48 ml 20.0 mmol) in THF (10 ml) was added dropwise over 30 min. After stirring for 2 h the THF was evaporated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, washed with water, 2M HCl, brine, dried (MgSO4), and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/hexane/ethyl acetate 9:9:2) to afford the product as a pale yellow oil. (2.08 g, 60%). 1NMR (300 MHz, CDCl3) 7.49-7.23 (4H, m), 6.97 (1H, d), 5.45 (1H, d), 4.30 (2H, m), 2.77 (2H, m), 2.47 (3H, s), 1.97 (3H, s) 1.67 (6H, m), 1.47 (8H, m), 1.34 (3H, t).

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with water, 2M HCl, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash column chromatography (silica, DCM/hexane/ethyl acetate 9:9:2)

Sources & evidence

ORD record
ord-6b6dd68230a841b594ade6c6b9545d22
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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