Acetic Anhydride → HCID 10324706, compound

HRID 1715368Notes

Reaction equation

HRID 1715368 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:29][C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])=[C:6]2[C:10]=1[CH2:9][N:8]([CH:11]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)[CH2:12][C:13](=[O:16])[NH:14][OH:15])[C:7]2=[O:28].[C:35](OC(=O)C)(=[O:37])[CH3:36]>CC#N>[C:35]([O:15][NH:14][C:13]([CH2:12][C@@H:11]([N:8]1[C:7](=[O:28])[C:6]2[C:10](=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:29][C:30]([CH:32]2[CH2:33][CH2:34]2)=[O:31])[CH2:9]1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)=[O:16])(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23567221HCID 23567221, compound

Product 1

HCID 10324706HCID 10324706, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of cyclopropanecarboxylic acid {7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (0.45 g, 92 mmol) in CH3CN (50 ml) was added acetic anhydride (0.1 ml, 92 mmol) at room temperature. The mixture was stirred overnight. The solvent was removed in vacuo and the resulted solid was stirred with ether (10 ml) for 2 hrs. The suspension was filtered and the solid was dried in oven to give (1R)-cyclopropanecarboxylic acid {2-[2-acetoxycarbamoyl-1-(3-ethoxy-4-methoxy-phenyl)-ethyl]-7-chloro-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (0.4 g, 80%): mp 139-141° C.; 1HNMR (CDCl3): δ 0.85-0.92 (m, 2H, c-CH2), 1.05-1.11 (m, 2H, c-CH2), 1.43 (t, J=7.5 Hz, 3H, OCH2CH3), 1.62-1.68 (m, 1H, c-CH), 2.12 (s, 3H, CH3), 3.02 (dd, J=5, 16 Hz, 1H, CHH), 3.50 (dd, J=5, 16 Hz, 1H, CHH), 3.85 (s, 3H, OCH3), 4.08 (q, J=7.5 Hz, 2H, OCH2CH3), 4.12 (d, J=17 Hz, 1H, CHH), 4.38 (d, J=17 Hz, 1H, CHH), 5.61-5.65 (m, 1H, CHN), 6.81-6.94 (m, 3H, Ar), 7.31 (d, J=10 Hz, 1H, Ar), 8.38 (d, J=10 Hz, 1H, Ar), 10.41 (s, 1H); 13C NMR (CDCl3): 9.0, 9.1, 15.3, 16.7, 18.7, 36.8, 48.2, 54.4, 56.5, 65.2, 112.2, 112.8, 119.7, 119.8, 120.2, 122.4, 131.1, 133.5, 137.2, 139.8, 149.3, 150.1, 167.0, 169.0, 170.0, 173.5; Anal. Calcd. for C26H28ClN3O7: C, 58.92; H, 5.33; N, 7.93. Found: C, 58.58; H, 5.00; N, 7.76.

Workup

  1. customThe solvent was removed in vacuo
  2. stirringthe resulted solid was stirred with ether (10 ml) for 2 hrs
  3. filtrationThe suspension was filtered
  4. customthe solid was dried in oven

Sources & evidence

ORD record
ord-b4771424fb8d40bb9f8f308ad6417665
Source dataset
uspto-grants-2010_09
Patent number
US07799819B2

Reaction notes

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