4-Acetylbenzoic Acid → HCID 67482692, compound

HRID 1817763Notes

Reaction equation

HRID 1817763 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.[C:14]([O:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)CCl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:22][CH2:21][CH2:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:23])=[O:10])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 114704-Acetylbenzoic AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 67482692HCID 67482692, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Acetylbenzoic acid (2.45 g, 14.9 mmol), beta-alanine t-butyl ester hydrochloride (4.0 g, 22 mmol), DIEA (3.9 ml, 22 mmol) and DMAP (100 mg) were dissolved in DCM (100 ml). EDC hydrochloride (3.5 g, 18 mmol) was added in portions. Additional EDC (0.7 g) was added one hour later to complete the reaction. After a total of 3 hours, the reaction was partitioned between ethyl acetate and 0.5 N HCl. The organic layer was washed with 0.5 N HCl 3×, 5% K2CO3 2×, brine 2×. Evaporation of solvent, and chromatography over SiO2 (10-20% ethyl acetate in DCM) afforded tert-butyl N-(4-acetylbenzoyl)-β-alaninate as a while solid. NMR (500 MHz, CD3OD) δ: 1.44 (s, 9H); 2.57 (t, J=7.0 Hz, 2H); 2.63 (s, 3H); 3.61 (t, J=7.0 Hz, 2H); 7.89 (d, J=8.5 Hz, 2H); 8.05 (d, J=8.5 Hz, 2H).

Workup

  1. customthe reaction
  2. customAfter a total of 3 hours, the reaction was partitioned between ethyl acetate and 0.5 N HCl
  3. washThe organic layer was washed with 0.5 N HCl 3×, 5% K2CO3 2×, brine 2×
  4. customEvaporation of solvent, and chromatography over SiO2 (10-20% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-86518bad40dd400997376bd18d9356b7
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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