Methanol → 3-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoic acid

HRID 853631ノート

反応式

HRID 853631 の反応式
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][S:6][CH:7]1[C:11]2[C:12]([O:21][CH3:22])=[C:13]3[C:18](=[C:19]([OH:20])[C:10]=2[C:9](=[O:23])[N:8]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:17]=[CH:16][CH:15]=[CH:14]3.O.CO.[Li+].[OH-]>C1COCC1>[F:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:8]2[C:9](=[O:23])[C:10]3[C:19]([OH:20])=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[N:17]4)=[C:12]([O:21][CH3:22])[C:11]=3[CH:7]2[S:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962Water2 回HCID 3939Lithium HydroxideHCID 10479199methyl 3-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoate

生成物 1

HCID 100034673-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 23 (150 mg, 0.329 mmol) in 3.29 mL of a 1:2:3 solution of H2O:MeOH:THF was stirred with LiOH. H2O (69 mg, 1.65 mmol) for 1 hour when LCMS demonstrated complete conversion of starting materials to product. The reaction mixture was dried under reduced pressure and the residue was suspended in water and the pH was adjusted to 11 with aqueous 1N NaOH solution. The aqueous layer was washed with EtOAc twice. The pH of the aqueous layer was then adjusted to 5 using 1N HCl and the product was extracted with CH2Cl2 under continuous extraction conditions. The organic layer was dried in vacuo to yield the product 24 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 2.1 (s, 1H), 2.25-2.45 (m, 4H), 4.04 (s, 3H), 4.43 (d, 1H, J=15 Hz), 5.32 (dd, 1H, J=3, 14 Hz), 5.49 (s, 1H), 7.03 (t, 2H, J=9 Hz), 7.35 (dd, 2H, J=5, 8 Hz), 7.57 (dd, 1H, J=4, 8 Hz), 8.52 (dd, 1H, J=2, 8 Hz), 8.98 (dd, 1H, J=2, 5 H); 13C NMR (75 MHz, CD3OD) δ 21.4, 33.6, 41.9, 61.8, 61.9, 112.3, 115.7, 116.0, 123.1, 125.0, 126.5, 130.4, 130.5, 131.8, 131.8, 139.3, 142.6, 148.3, 149.6, 162.4 (d, J=245 Hz), 167.2, 175.3; 19F NMR (282.6 MHz, CDCl3) δ 62.6; EI MS (m/z) 441.4 [M−H]−, 883.1 [2M−2H]−.

後処理

  1. customThe reaction mixture was dried under reduced pressure
  2. washThe aqueous layer was washed with EtOAc twice
  3. extractionthe product was extracted with CH2Cl2 under continuous extraction conditions
  4. customThe organic layer was dried in vacuo

出典と根拠

ORDレコード
ord-5f13f85d327e40cb942f6d575222da05
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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