Lithium Hydroxide → HCID 57920040、化合物

HRID 19169ノート

反応式

HRID 19169 の反応式
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

参加物

4

反応物 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

生成物 1

HCID 57920040HCID 57920040、化合物収率 96.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-54935154868941a980689988b23bd213
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

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