Potassium Bromide → HCID 54463444, compound

HRID 1871694Notes

Reaction equation

HRID 1871694 reaction equation
C(C1N(CC(OC)=O)C(=O)C(OCCC2C=CC=CC=2)=C(N=C=O)C=1)C1C=CC=CC=1.[K+].[Br-].NC1C(=O)N(C(C)C(OC)=O)C=CC=1.[CH3:48][O:49][C:50](=[O:71])[CH:51]([N:53]1[CH:58]=[CH:57][CH:56]=[C:55]([NH:59][C:60]([O:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)=[O:61])[C:54]1=[O:70])C>[Pd].CO>[CH2:63]([O:62][C:60]([NH:59][C:55]1[C:54](=[O:70])[N:53]([CH2:51][C:50]([O:49][CH3:48])=[O:71])[CH:58]=[CH:57][CH:56]=1)=[O:61])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

7

Reactant 4

HCID 253877Potassium BromideHCID 18469010HCID 18469010, compoundHCID 18469014HCID 18469014, compoundHCID 86650106HCID 86650106, compound

Product 1

HCID 54463444HCID 54463444, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl [6-benzyl-1,2-dihydro-2-oxo-3-(2-phenylethoxy)-carbonylamino-1-pyridyl]acetate (49i), was isolated (88%) as a colorless solid: mp. 130-133° C.; IR (KBr) 3363, 1746, 1732, 1651, 1604, 1515, 1368, 1231, 1212, 1185; 1H NMR (CDCl3) δ 8.00 (1H, d, J=7.0), 7.68 (1H, s), 7.36-7.10 (10H, m), 6.15 (1H, d, J=7.6), 4.7 (2H, s), 4.38 (2H, t, J=7.0), 3.88 (2H, s), 3.67 (3H, s), 2.98 (2H, t, J=7). ##STR132## 2(S) Methyl 2[3-amino-1,2-dihydro-2-oxo-1-pyridyl]propionate (50a). A mixture of 2(S) methyl-2[3-benzyloxycarbonylamino-1,2-dihydro-2-oxo-1-pyridyl)propionate (49a) (2.75 g, 8.33 mmol), methanol (100 ml), and 10% palladium on carbon (300 mg) was stirred under an atmosphere of hydrogen for 30 min. The mixture was filtered and concentrated to afford 1.63 g (100%) of a colorless solid: 1H NMR (d6 -DMSO) δ 8.35 (1H, brs), 7.46 (1H, d), 7.22 (1H,d), 6.29 (1H, t), 5.22 (1H, q), 3.63 (3H, s), 1.55 (3H, d).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b9356699d8ca42fcafdfb379ea5e5c41
Source dataset
uspto-grants-2000_08
Patent number
US06103711

Reaction notes

Loading…