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

HRID 1602664Notes

Reaction equation

HRID 1602664 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

##STR52## 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, 3 H), 4.86 (s, 2 H), 5.18 (s, 2 H), 6.24 (d, J=7.9 Hz, 1 H), 7.31-7.41 (m, 6 H), 7.94 (br s, 1 H).

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-a15b52fb86244de7b7cc52de4262f23b
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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