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Hydrochloric Acid → (S)-2-[4-(2,6-difluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide

HRID 19125
ノート
印刷プレビュー

反応式

HRID 19125 の反応式
CC1(C)[O:6][C@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:37])[C@@H:15]([N:20]3[CH2:24][C:23]([O:25][C:26]4[C:31]([F:32])=[CH:30][CH:29]=[C:28]([O:33][CH3:34])[C:27]=4[F:35])=[CH:22][C:21]3=[O:36])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:9]2)[CH2:4][O:3]1.Cl>O1CCCC1.C(OCC)(=O)C>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:37])[C@@H:15]([N:20]2[CH2:24][C:23]([O:25][C:26]3[C:31]([F:32])=[CH:30][CH:29]=[C:28]([O:33][CH3:34])[C:27]=3[F:35])=[CH:22][C:21]2=[O:36])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 57920095(S)-2-[4-(2,6-difluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide

生成物 1

HCID 57920178(S)-2-[4-(2,6-difluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide収率 91%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (S)-2-[4-(2,6-difluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (prepared in Example 118, 0.163 g, 0.30 mmol) in tetrahydrofuran (15 mL) was treated with 2N aqueous hydrochloric acid (7.5 mL). The reaction mixture was stirred for 3.5 h at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, a saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified by ISCO column chromatography (Teledyne Isco RediSep Flash Column 12 g, 30% to 100%, (9:1 dichloromethane:methanol)/hexanes) which afforded (S)-2-[4-(2,6-difluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (0.135 g, 90%) as an off-white solid: HR-ES-MS m/z calculated for C23H28F2N4O6, [M+H]+ 495.205 observed 495.205; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (d, J=6.4 Hz, 3H), 0.93 (d, J=6.4 Hz, 3H), 1.43 (br. s., 1H), 1.49-1.67 (m, 1H), 1.67-1.87 (m, 1H), 3.18-3.32 (m, 2H), 3.69-3.86 (m, 2H), 3.87 (s, 3H), 4.09 (dd, J=13.6, 2.7 Hz, 1H), 4.27 (d, J=18.7 Hz, 1H), 4.63 (d, J=18.7 Hz, 1H), 4.71 (t, J=4.8 Hz, 1H), 4.81-4.91 (m, 1H), 4.94 (d, J=4.8 Hz, 1H), 5.06 (s, 1H), 6.40 (br. s., 1H), 7.09-7.24 (m, 1H), 7.24-7.38 (m, 1H), 7.53 (br. s., 1H), 10.79 (br. s., 1H).

後処理

  1. washwashed with saturated sodium bicarbonate
  2. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customthe residue purified by ISCO column chromatography (Teledyne Isco RediSep Flash Column 12 g, 30% to 100%, (9:1 dichloromethane:methanol)/hexanes) which

出典と根拠

ORDレコード
ord-955c5eb1bdbe43de98ef44f8367b1cf2
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741327B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート