Acetic Anhydride → HCID 10414018, compound

HRID 1444555Notes

Reaction equation

HRID 1444555 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH2:20]2)[CH2:13][CH2:14][N:15]([CH:17]=[O:18])[OH:16])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(#N)C>[C:35]([O:16][N:15]([CH2:14][CH2:13][C@@H:12]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH2:20]1)[C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[CH:17]=[O:18])(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11754433HCID 11754433, compound

Product 1

HCID 10414018HCID 10414018, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1R)-N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-3-(N-formyl-N-hydroxy-amino)-propyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-isobutyramide (300 mg, 0.64 mmol) in acetonitrile (6 mL) was added acetic anhydride (0.1 mL, 1 mmol) at room temperature. After 4 h, the solvent was removed in vacuo and the residue was purified by chromatography (Silica Gel) to give (1R)-N-{2-[3-(N-acetoxy-N-formyl-amino)-1-(3-ethoxy-4-methoxy-phenyl)-propyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-isobutyramide as a white solid (0.21 g, 64% yield): mp: 72-74° C. 1H NMR (DMSO-d6) δ 1.17 (d, J=7 Hz, 6H, 2CH3), 1.31 (t, J=7 Hz, 3H, CH3), 2.19 (s, 3H, CH3), 2.32-2.50 (m, 2H, CH2), 2.59-2.68 (m, 1H, CH), 3.60-3.67 (m, 2H, CH2), 3.73 (s, 3H, CH3), 3.99-4.09 (m, 3H, NCHH, CH2), 4.56 (d, J=17 Hz, 1H, NCHH), 5.30-5.38 (m, 1H, NCH), 6.88-6.93 (m, 3H, Ar), 7.18 (d, J=8 Hz, 1H, Ar), 7.50 (t, J=8 Hz, 1H, Ar), 8.11 (s, 1H, CH), 8.29 (d, J=8 Hz, 1H, Ar), 10.47 (s, 1H, NH); 13C NMR (DMSO-d6) δ 14.69, 18.01, 19.16, 28.87, 35.94, 45.87, 46.13, 51.18,55.45,63.80, 111.96,112.32,116.55, 117.55, 119.76, 131.30,132.79,137.14, 142.32, 147.99, 148.59, 157.50, 163.00, 167.31, 168.57, 174.94; Anal Calcd for C27H33N3O7+0.2H2O: C, 62.95; H, 6.53; N, 8.16; H2O, 0.70. Found: C, 62.81; H, 6.63; N, 7.92; H2O, 0.59.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (Silica Gel)

Sources & evidence

ORD record
ord-f18e4097104f49e186d9dbac0d6ff495
Source dataset
uspto-grants-2010_02
Patent number
US07662847B2

Reaction notes

Loading…