Lithium hydroxide, monohydrate → HCID 9827393, 화합물

HRID 987518노트

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HRID 987518 반응식
[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]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrate2회HCID 11478104HCID 11478104, 화합물

생성물 1

HCID 9827393HCID 9827393, 화합물수율 87.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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+).

후처리

  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.

출처 및 근거

ORD 기록
ord-1d6460c884e84e5ea5d2add0d814a1ae
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632814B1

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