Acetic Acid → HCID 135659593, compound

HRID 2289268Notes

Reaction equation

HRID 2289268 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH:17]=[CH:18][C:19]4[CH:40]=[CH:39][C:22]([C:23]([NH:25][C@H:26]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:24])=[CH:21][CH:20]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.C(O)(=O)C>[Pd].C(O)C>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]([NH:25][C@H:26]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:24])=[CH:39][CH:40]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 136093149HCID 136093149, compound

Product 1

HCID 135659593HCID 135659593, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of diethyl N-(4-(2-(1.2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)vinyl)benzoyl)-L-glutamate (0.16 g, 0.29 mmol) and 10% palladium on carbon (0.10 g) in ethanol (100 ml) was shaken under hydrogen (40 psi) overnight. Ethanol (80 ml) and acetic acid (20 ml) were added and the mixture was hydrogenated (40 psi) for 1 day. The solution was filtered, concentrated in vacuo, and the residue and catalyst were recombined in acetic acid (40 ml) and hydrogenated over the weekend. The solution was filtered, concentrated in vacuo and the product twice filtered from a small volume of methanol to give diethyl N-(4-(2-(1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)ethyl)benzoyl)-L-glutamate (0.10 g). 4NMR (DMSO-d6, 300 MHz) δ: 1.16 (t, J=7 Hz, 3H, ester CH3), 1.19 (t, J=7 Hz, 3H, ester CH3), 1.90-2.18 (m, 2H, gluCH2), 2.43 (s, 3H, C3 --CH3), 2.44 (t, J=7.5 Hz, 2H, gluCH2), 3.03-3.22 (m, 4H, ArCH2 's), 4.04 (q, J=7 Hz, 2H, ester CH2), 4.10 (q, J=7 Hz, 2H, ester CH2), 4.37-4.47 (m, 1H, gluCH), 7.40 (d, J=8 Hz, 2H, Ar), 7.54 (dd, J=8, 1.5 Hz, 1H, Ar), 7.57 (d, J=8.5 Hz, 1H, Ar), 7.80 (d, J=8 Hz, 2H, Ar), 7.95 (d, J=8 Hz, 1H, Ar), 8.20 (d, J=9 Hz, 1H, Ar), 8.65 (d, J=7.5 Hz, 1H, gluNH), 9.72 (s, 1H, Ar), 12.51 (br s, 1H, N2H). Mass spectrum (CI-CH4): 544 (M+1, 4.2%). Anal. Calculated for C31H33N3O6.1/10H2O: C, 68.27; H, 6.14; N, 7.70. Found: C, 68.34; H, 6.10; N, 7.68.

Workup

  1. customfor 1 day
  2. filtrationThe solution was filtered
  3. concentrationconcentrated in vacuo
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. filtrationthe product twice filtered from a small volume of methanol

Sources & evidence

ORD record
ord-500910ecfdf84b35b6742cee84c383da
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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