Acetic Anhydride → HCID 136383507, compound

HRID 2110591Notes

Reaction equation

HRID 2110591 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17][O:18][CH3:19])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:20])[C:3]=1[C:21]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][C:24]=2[S:23](=[O:40])(=[O:39])[N:22]=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>N1C=CC=CC=1>[C:41]([N:17]([O:18][CH3:19])[C:5]1([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:21]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:30][C:24]=3[S:23](=[O:39])(=[O:40])[N:22]=2)[C:4]1=[O:20])(=[O:43])[CH3:42]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 135885149HCID 135885149, compound

Product 1

HCID 136383507HCID 136383507, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the product from Example 18B (23 mg, 0.04 mmol) in pyridine (0.5 mL) was added acetic anhydride (38 μL, 0.4 mmol). The reaction solution was stirred at room temperature for 18 h. After which, the solution was concentrated in vacuo. The resulting residue was taken up ethyl acetate (2 mL) and washed with aqueous 1 N HCl (2×1 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (1%→3%→5% methanol/dichloromethane) afforded the title compound as a yellow solid (17 mg, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.34-0.52 (m, 1H), 0.58-0.76 (m, 6H), 0.88-1.04 (m, 1H), 1.20-1.37 (m, 2H), 1.50 (s, 9H), 2.04 (s, 3H), 7.53 (t, J=7.54 Hz, 2H), 7.62-7.77 (m, 3H), 8.07-8.17 (m, 2H), 9.89 (s, 1H), 13.49 (s, 1H); MS m/z 613.1 (M+H)+.

Workup

  1. concentrationAfter which, the solution was concentrated in vacuo
  2. washwashed with aqueous 1 N HCl (2×1 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8c921169f16438ba99682a01347ec27
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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