Lithium Hydroxide → HCID 57920040, 화합물

HRID 19169노트

반응식

HRID 19169 반응식
C([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:35])[C@@H:13]([N:18]2[CH2:22][C:21]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]4[CH2:32][CH2:31]4)[C:25]=3[F:33])=[CH:20][C:19]2=[O:34])[CH2:14][CH:15]([CH3:17])[CH3:16])=[N:7]1)C.[OH-].[Li+]>O1CCCC1>[CH:30]1([C:26]2[C:25]([F:33])=[C:24]([CH:29]=[CH:28][CH:27]=2)[O:23][C:21]2[CH2:22][N:18]([C@@H:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:12]([NH:11][C:8]3[CH:9]=[CH:10][N:6]([CH2:5][C:4]([OH:36])=[O:3])[N:7]=3)=[O:35])[C:19](=[O:34])[CH:20]=2)[CH2:32][CH2:31]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 57920089(3-{(S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoylamino}-pyrazol-1-yl)-acetic acid ethyl ester

생성물 1

HCID 57920040HCID 57920040, 화합물수율 96.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (3-{(S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoylamino}-pyrazol-1-yl)-acetic acid ethyl ester (prepared as in Example 148, 0.130 g, 0.26 mmol) in tetrahydrofuran (5 mL) was added an aqueous lithium hydroxide solution (0.5N, 2 mL). The resulting mixture was stirred at room temperature for 3 h. The solvents were evaporated and the residue neutralized with 1N aqueous hydrochloric acid, extracted with ethyl acetate. The combined organic layers were washed with water, saturated sodium chloride solution and dried over sodium sulfate. The mixture was filtered and evaporated which afforded (3-{(S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoylamino}-pyrazol-1-yl)-acetic acid (0.118 g, 96%) as a white solid: HR-ES-MS m/z calculated for C24H27FN4O5 [M+H]+ 471.2038 observed 471.2036; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.72-0.81 (m, 2H), 0.90 (d, J=6.3 Hz, 3H), 0.93 (d, J=6.3 Hz, 3H), 0.97-1.06 (m, 2H), 1.37-1.51 (m, 1H), 1.52-1.65 (m, 1H), 1.65-1.82 (m, 1H), 2.00-2.15 (m, 1H), 4.21 (d, J=18.4 Hz, 1H), 4.59 (d, J=18.4 Hz, 1H), 4.62 (s, 2H), 4.86 (s, 1H), 4.85-4.93 (m, 1H), 6.42 (d, J=2.0 Hz, 1H), 6.94 (t, J=6.9 Hz, 1H), 7.15 (t, J=7.8 Hz, 1H), 7.21-7.31 (m, 1H), 7.54 (d, J=2.0 Hz, 1H), 10.75 (s, 1H).

후처리

  1. customThe solvents were evaporated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water, saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationThe mixture was filtered
  6. customevaporated which

출처 및 근거

ORD 기록
ord-54935154868941a980689988b23bd213
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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