Acetic Acid → (+/-)-[10-(4-Chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid

HRID 857323ノート

反応式

HRID 857323 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17]([CH3:19])=[O:18])[N:10]3[CH2:20][CH2:21][CH2:22][CH:23]([CH2:24][C:25]([O:27]CC)=[O:26])[C:9]=23)=[CH:4][CH:3]=1.C1COCC1.CO.[Li+].[OH-].CC(O)=O>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17]([CH3:19])=[O:18])[N:10]3[CH2:20][CH2:21][CH2:22][CH:23]([CH2:24][C:25]([OH:27])=[O:26])[C:9]=23)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 90857561(+/-)-Ethyl [10-(4-chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-9-yl]acetate

生成物 1

HCID 21867520(+/-)-[10-(4-Chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of the ester of Step 13 in a THF/MeOH (3:1) mixture at r.t. was added 1N LiOH (aqueous solution). The reaction mixture was stirred at r.t. for 2 hours and AcOH (0.5 mL) and brine (5 mL) were added. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was swished in EtOAc/hexanes to give the desired acid as a white solid. Each isomer from Step 13 was hydrolyzed under these conditions. From the less polar diastereomer of Step 13: 1H NMR (methanol-d4) δ 7.65 (1H, d), 7.61 (1H, d), 7.51–7.35 (5H, m), 4.37–4.29 (1H, m), 4.09–4.02 (1H, m), 3.79–3.71 (1H, m), 2.40 (1H, dd), 2.24 (3H, s), 2.23–1.91 (5H, m). MS (−APCI) m/z 400.2 M-H)+.

後処理

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-3dc39eb59842496ead6dfa0603a4fc29
出典データセット
uspto-grants-2006_12
特許番号
US07144913B2

反応ノート

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