Pyridine → Tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate

HRID 1919903Notes

Reaction equation

HRID 1919903 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl.CCOC(C)=O>[C:28]([NH:2][CH2:3][CH:4]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:20][CH:21]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67496911Tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride

Product 1

HCID 57611947Tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl 4-[1-(aminomethyl)-2-methoxy-2-oxoethyl]benzoate hydrochloride (600 mg, 1.90 mmol) in CH2Cl2 were added pyridine (0.38 mL, 4.75 mmol) and acetyl chloride (0.20 mL, 2.85 mmol). After stirring for 2 h at room temperature, the reaction mixture was diluted with EtOAc, washed (sat. CuSO4, sat. NaHCO3, brine), dried (MgSO4), and concentrated. Flash chromatography on silica gel (50-100% EtOAc/hexanes) afforded tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate as a thick, colorless oil. 1H NMR (CDCl3) δ7.94 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.2 Hz, 2H), 5.87 (t, J=5.5 Hz, 1H), 3.96 (dd, J=8.8, 5.9 Hz, 1H), 3.71-3.60 (m, 2H), 3.67 (s, 3H), 1.93 (s, 3H), 1.57 (s, 9H). MS (ESI) calcd [M+H]+ 322.1, found 322.1.

Workup

  1. washwashed (sat. CuSO4, sat. NaHCO3, brine)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4bab774209334f5caf3137bca1cb1913
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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