Potassium Bromide → HCID 18469010, compound

HRID 1182523Notes

Reaction equation

HRID 1182523 reaction equation
[NH2:1][C:2]1[C:3](=[O:20])[N:4]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:5](CC2C=CC=CC=2)=[CH:6][CH:7]=1.[K+].[Br-].[CH3:23]OC(=O)CN1C(CCC2C=CC=CC=2)=CC=C(N)C1=O>>[NH2:1][C:2]1[C:3](=[O:20])[N:4]([CH:15]([CH3:23])[C:16]([O:18][CH3:19])=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 253877Potassium Bromide2×HCID 18690853HCID 18690853, compoundHCID 22104295HCID 22104295, compound

Product 1

HCID 18469010HCID 18469010, compound

Procedure

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). The following compounds were prepared in a similar manner: Methyl [3-amino-6-benzyl-1,2-dihydro-2-oxo-1-pyridyl]acetate (50b). 100% yield as a grey solid: mp. 134-6° C.; IR (KBr) 3418, 3312, 1723, 1658, 1596, 1548, 1435, 1290, 1245, 1011; 1H NMR (d6-DMSO) δ 7.25 (5H, m), 6.45 (1H, d, J=7.4), 5.92 (1H, d, J=7.4), 5.00 (2H, s), 4.63 (2H, s), 3.88 (2H, s), 3.51 (3H, s). Methyl[3-amino-1,2-dihydro-2-oxo-6-phenethyl-1-pyridyl]acetate (50c). 99% yield as a viscous oil: IR (KBr) 3456, 341, 2953, 1745, 1649, 1600, 1548, 1219;

Workup

  1. customThe following compounds were prepared in a similar manner

Sources & evidence

ORD record
ord-e2d31cdea52d44f0942d8e49fbc35296
Source dataset
uspto-grants-2007_10
Patent number
US07288624B2

Reaction notes

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