Acetic Anhydride → HCID 67445382, compound

HRID 1667605Notes

Reaction equation

HRID 1667605 reaction equation
O[NH:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]([O:9][CH:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[C:17]([O:25][CH2:26][CH3:27])[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[NH:4].C(OC(=O)C)(=O)C.[H][H]>C(O)(=O)C.[Pd]>[C:11]([OH:13])(=[O:12])[CH3:10].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:23])[CH3:24])=[C:17]([O:25][CH2:26][CH3:27])[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:28][CH:29]=1)(=[NH:2])[NH2:4]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 178418361HCID 178418361, compoundHCID 178466781HCID 178466781, compound

Product 1

HCID 67445382HCID 67445382, compoundYield 181.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 9B (575 mg, 1.43 mmol) in acetic acid (14 mL) was added acetic anhydride (0.155 mL, 1.64 mmol) and 10% Pd/C (90 mg). The mixture was hydrogenated with a hydrogen balloon at rt for 3.0 h. After removal of solvent, 9C (580 mg, 100% yield) was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.24 (d, J=6.16 Hz, 6H) 1.30 (t, J=7.03 Hz, 3H) 1.69 (s, 3H) 3.66 (s, 3H) 4.00 (q, J=7.03 Hz, 2H) 4.46-4.50 (m, 1H) 6.09 (s, 1H) 6.90 (d, J=8.35 Hz, 1H) 6.97-7.14 (m, 4H) 7.72 (d, J=9.23 Hz, 2H). LC-MS 387 (M+H)+.

Workup

  1. customAfter removal of solvent

Sources & evidence

ORD record
ord-cec498cffcc547a38cda3ffdf0e8969b
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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