HCID 18468955, compound → HCID 57097216, compound

HRID 2257407Notes

Reaction equation

HRID 2257407 reaction equation
[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]([CH2:12][C:13]([NH:15][CH:16]3[CH2:20][C:19](=[O:21])[O:18][CH:17]3[O:22]CC3C=CC=CC=3)=[O:14])[C:10](=[O:11])[C:5]=2[NH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]([CH2:12][C:13]([NH:15][C@H:16]([CH:17]=[O:22])[CH2:20][C:19]([OH:21])=[O:18])=[O:14])[C:10](=[O:11])[C:5]=2[NH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18468955HCID 18468955, compound

Product 1

HCID 57097216HCID 57097216, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 42 (131 mg, 0.33 mmol), in methanol (50 ml) and 10% palladium on carbon (100 mg) was stirred vigorously under an atmosphere of hydrogen for 2 h. An additional quantity of catalyst (100 mg) was added and the mixture hydrogenated for a further 2 h. The mixture was filtered through a 0.2 μM nylon membrane, and concentrated. The residue was recrystallised from methanol/diethyl ether to afford 79 mg (78%) of 43 as a hygroscopic white solid: mp. 222°-226° C.; (decomp.); [α]D32 +0.5 (c 0.02, MeOH); IR (KBr) 3282, 1680, 1558, 1425 1275; 1H NMR (CD3OD) δ 8.03 (1H, s), 7.18 (1H, d, J=0.7), 4.79-4.74 (2H, m), 4.63-4.59 (1H, 2×d, J=3.6), 4.36-4.25 (1H, m), 2.78-2.39 (2H, m), 2.24 (3H, d, J=0.7). Anal. Calcd for C13H14N4O5. 1.4H2O: C, 47.10; H, 5.12; N, 16.90. Found: C, 47.00; H, 4.79; N, 16.59. FABMS m/e 307, 306 (M+), 244, 207, 190, 152, 115 (100%). ##STR101##

Workup

  1. filtrationThe mixture was filtered through a 0.2 μM nylon membrane
  2. concentrationconcentrated
  3. customThe residue was recrystallised from methanol/diethyl ether

Sources & evidence

ORD record
ord-e12625e747df4e0b960311be41527f8e
Source dataset
uspto-grants-1997_08
Patent number
US05656627

Reaction notes

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