Sodium Hydroxide → HCID 9938977, compound

HRID 987519Notes

Reaction equation

HRID 987519 reaction equation
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:19]([CH3:26])[CH2:20][C:21]([O:23]CC)=[O:22])[CH:17]=2)[N:12]([C:27](=[O:48])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH3:45])=[O:37])=[C:31]([O:46][CH3:47])[CH:30]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:19]([CH3:26])[CH2:20][C:21]([OH:23])=[O:22])[CH:17]=2)[N:12]([C:27](=[O:48])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH3:45])=[O:37])=[C:31]([O:46][CH3:47])[CH:30]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18008963HCID 18008963, compound

Product 1

HCID 9938977HCID 9938977, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A stirred solution of ethyl 3-(4-benzoyl-1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinoxalin-6-yl)-butanoate [0.124 g, Reference Example 16(a)] in methanol (5 ml) was treated with sodium hydroxide solution (764 μl, 15%). The resulting mixture was heated to reflux for 30 minutes, then cooled to 40° C. and then evaporated (40 mbar, 40° C.). The residue was treated with distilled water (40 ml) and the aqueous solution was washed three times with ether (20 ml), then treated with hydrochloric acid (4 ml, 1M) and then extracted three times ethyl acetate (25 ml). The combined extracts were dried over magnesium sulfate then evaporated to dryness (40 mbar, 40° C.). The crude residue (91 mg) was subjected to preparative thin layer chromatography on silica(20×20 cm plates, 0.25 mm thickness) eluting with a mixture of dichloromethane and methanol (9:1, v/v) to give the title compound as a white powder (15 mg). 1H NMR (400 MHz, (CD3)2SO, at a temperature of 373° K.]: δ0.92 (d, J=7 Hz, 3H); 2.16 (d, J=7.5 Hz, 2H); 2.27(s, 3H); 2.80 to 3.05 (m, 1H); 3.84 (s, 3H); 3.94 (m, 2H); 3.96 (s, 2H); 4.01 (m, 2H); 6.60 (broad s, 1H); 6.76 (broad d, J=8 Hz, 1H); 6.88 (broad s, 1H); 6.95 to 7.05 (m, 2H); 7.10 to 7.20 (m, 4H); 7.33 (broad t, J=7.5 Hz, 2H); 7.40 (broad t, J=7.5 Hz, 1H); 7.56 (d, J=8 Hz, 1H); 7.68 (broad d, J=8 Hz, 1H); 8.04 (d, J=8.5 Hz, 1H); 8.23 (broad s, 1H); 8.29 (broad s, 1H). MS (ES): 621 (MH+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 30 minutes
  3. customevaporated (40 mbar, 40° C.)
  4. additionThe residue was treated with distilled water (40 ml)
  5. washthe aqueous solution was washed three times with ether (20 ml)
  6. additiontreated with hydrochloric acid (4 ml, 1M)
  7. extractionextracted three times ethyl acetate (25 ml)
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. customthen evaporated to dryness (40 mbar, 40° C.)
  10. washeluting with a mixture of dichloromethane and methanol (9:1

Sources & evidence

ORD record
ord-6267f527e86c49c7b031a4f497e93ebb
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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