Acetic Anhydride → HCID 136383518, compound

HRID 2110615Notes

Reaction equation

HRID 2110615 reaction equation
[CH2:1]([NH:8][C:9]1([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:44](OC(=O)C)(=[O:46])[CH3:45].C(N(CC)CC)C>ClC(Cl)C>[CH2:1]([N:8]([C:9]1([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37])[C:44](=[O:46])[CH3:45])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 135885156HCID 135885156, compound

Product 1

HCID 136383518HCID 136383518, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of the product of Example 74G (20 mg, 0.032 mmol) in dichloroethane (0.5 mL), acetic anhydride (5 μL, 0.048 mmol) and triethylamine (13 μL, 0.096 mmol) were added. The reaction solution was heated at 75° C. for 96 h. After cooling to room temperature, the solution was concentrated in vacuo. The resulting residue was dissolved in methanol (0.5 mL) and treated with excess of K2CO3 for 30 min. The mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was taken up in ethyl acetate (1 mL), washed with aqueous 1 N HCl, dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (1%→2%→3% methanol/dichloromethane) afforded the title compound as a brown solid (5 mg, 24%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.25-0.42 (m, 1H), 0.47 (s, 9H), 0.73-0.96 (m, 1H), 1.68-2.05 (m, 5H), 3.02 (s, 3H), 5.06 (d, J=18.02 Hz, 1H), 5.24-5.42 (m, 1H), 7.27-7.61 (m, 10H), 7.83 (d, J=6.99 Hz, 1H), 10.01 (s, 1H); MS m/z 665.2 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in methanol (0.5 mL)
  4. additiontreated with excess of K2CO3 for 30 min
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. washwashed with aqueous 1 N HCl
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54a9763ba5864c9eac2699d35fcfb88e
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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