Lithium hydroxide, monohydrate → HCID 9827393, compound

HRID 987518Notes

Reaction equation

HRID 987518 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])=[CH:30][CH:31]=3)[NH:26][CH2:25][CH2:24]2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].O.[OH-].[Li+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:30][CH:31]=3)[NH:26][CH2:25][CH2:24]2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 11478104HCID 11478104, compound

Product 1

HCID 9827393HCID 9827393, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro -quinoxalin-6-yl)-propanoate (0.16 g, Reference Example 1) in anhydrous ethanol (3 ml), at 25° C., was treated dropwise with a solution of lithium hydroxide monohydrate (22 mg) in distilled water (1 ml). After stirring for 4 hours at 25° C. a further portion (10 mg) of lithium hydroxide monohydrate was added and stirring was continued for 16 hours at 25° C. The reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C. and the residue was treated with distilled water (40 ml). The resulting solution was washed twice with diethyl ether (20 ml), then acidified to pH 3 by addition of hydrochloric acid (1.3 ml, 1N) and then extracted three times with ethyl acetate (25 ml). The combined organic extracts were washed twice with water (5 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. to give the title compound (132 mg) as a foamy solid. 1H NMR [400 Hz, (CD3)2SO]: δ2.2 (s, 3H); 2.5 (bq, 2H); 2.7 (broad t, 2H); 3.2 (broad s, 2H); 3.65 (broad s, 2H); 3.8 (s, 5H); 6.1 (broad s, 1H); 6.4 (broad s, 1H); 6.45 (broad s, 1H); 6.7 (very broad s, 1H); 6.9 (t, J=8 Hz, 1H); 7.15 (m, 3H); 7.8 (d, J=8 Hz, 1H); 8 (broad s, 1H); 8.45(s, 1H); 8.6(s, 1H); 12.1 (broad s, 1H. MS (LSIMS: glycerol+thioglycerol): 503 (MH+).

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C.
  3. additionthe residue was treated with distilled water (40 ml)
  4. washThe resulting solution was washed twice with diethyl ether (20 ml)
  5. additionacidified to pH 3 by addition of hydrochloric acid (1.3 ml, 1N)
  6. extractionextracted three times with ethyl acetate (25 ml)
  7. washThe combined organic extracts were washed twice with water (5 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-1d6460c884e84e5ea5d2add0d814a1ae
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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