Hydrochloric Acid → 3-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

HRID 322537Notes

Reaction equation

HRID 322537 reaction equation
Cl.C([O:6][C:7](=[O:28])[CH2:8][N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:10]1=[O:27])(C)(C)C>C(OCC)(=O)C>[CH3:15][C:14]1[N:9]([CH2:8][C:7]([OH:28])=[O:6])[C:10](=[O:27])[C:11]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10248693HCID 10248693, compound

Product 1

HCID 100186233-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled through a stirred suspension of 2-[6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl]acetic acid t-butyl ester (16-3; 12.3 g, 33 mmol) in ethyl acetate (250 ml) at −15° C. for 20 min. The resulting solution was allowed to warm to room temperature and was then stirred there for 3 h. After purging with argon, the bulk of the solvent was rotavapped off and ether added to the residue. The solid which precipitated was filtered off and washed with ether. The title compound 16-4 was thus obtained as a white fluffy powder: 1H NMR (CD3OD) δ 2.32 (s, 3H), 4.86 (s, 2H), 5.18 (s, 2H), 6.24 (d, J=7.9 Hz, 1H), 7.31-7.41 (m, 6H), 7.94 (br s, 1H).

Workup

  1. customAfter purging with argon
  2. additionether added to the residue
  3. customThe solid which precipitated
  4. filtrationwas filtered off
  5. washwashed with ether

Sources & evidence

ORD record
ord-906ee92e569040d18414fba422a1a90e
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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