HCID 136396880, compound → HCID 137194559, compound

HRID 2110596Notes

Reaction equation

HRID 2110596 reaction equation
C([O:8][NH:9][C:10]1([CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]([C:21]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([N:31]([S:38]([CH3:41])(=[O:40])=[O:39])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][C:24]=3[S:23](=[O:43])(=[O:42])[N:22]=2)[C:11]1=[O:44])C1C=CC=CC=1>OS(O)(=O)=O>[OH:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([NH:9][OH:8])([CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[C:11](=[O:44])[C:12]=1[C:21]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([N:31]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:30][C:24]=2[S:23](=[O:42])(=[O:43])[N:22]=1

Participants

3

Reactant 1

HCID 136396880HCID 136396880, compound

Product 1

HCID 137194559HCID 137194559, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of Example 53A (40 mg, 0.056 mmol) an in conc. H2SO4 (0.25 mL) was stirred at 25° C. for 1.5 h. The solution was quenched with water, neutralized to pH 7 with 1 N NaHCO3, and extracted with ethyl acetate. The organic extract was concentrated in vacuo. Column chromatography on silica (10% methanol/dichloromethane) afforded the title compound as a yellow solid (23 mg, 75%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.40-0.59 (m, 1H), 0.64 (dd, J=1.40, 6.62 Hz, 6H), 0.81-0.92 (m, 1H), 0.92-1.03 (m, 1H), 1.18 (t, J=7.17 Hz, 3H), 1.45-1.67 (m, 1H), 1.64-1.82 (m, 1H), 3.11 (s, 3H), 4.12 (q, J=6.99 Hz, 2H), 4.54 (s, 2H), 7.30-7.47 (m, 2H), 7.47-7.87 (m, 4H), 8.06 (d, 1H), 14.92-15.36 (br.s, 1H); MS m/z 621.0 (M+H)+.

Workup

  1. customThe solution was quenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6141b58a450a41bdba43d3c268315d51
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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