Thionyl Chloride → 9-benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione

HRID 1349499ノート

反応式

HRID 1349499 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:31])[C:11]([C:28](O)=[O:29])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:15](=[O:27])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:36][C:37]([Mg]Cl)([CH3:40])[CH2:38][CH3:39].CCOCC.S([O-])(O)(=O)=O.[K+]>O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[C:10](=[O:31])[C:11]([C:28](=[O:29])[C:37]([CH3:40])([CH3:36])[CH2:38][CH3:39])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:15](=[O:27])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 24386Thionyl ChlorideHCID 516920Potassium bisulfateHCID 230775239-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acidHCID 178467772HCID 178467772、化合物

生成物 1

HCID 230774849-benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

9-Benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid (200 mg) obtained in Example 219, Step 2 was suspended in tetrahydrofuran (6 ml), and triethylamine (0.07 ml) and thionyl chloride (0.037 ml) were added at room temperature with stirring. After stirring at room temperature for 10 min, the mixture was cooled to −78° C. and 1.0 M 1,1-dimethylpropylmagnesium chloride/ether solution was added dropwise. After further stirring at the same temperature for 20 min, 5% aqueous potassium hydrogen sulfate solution (5 ml) and ethyl acetate (6 ml) were added, and water (5 ml) was further added. The mixture was extracted twice with ethyl acetate-tetrahydrofuran (1:1, 30 ml each). The organic layer was dried and concentrated, and ethyl acetate was added to the residue. The obtained solid was collected by filtration to give 9-benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (59 mg).

後処理

  1. stirringAfter stirring at room temperature for 10 min
  2. stirringAfter further stirring at the same temperature for 20 min
  3. extractionThe mixture was extracted twice with ethyl acetate-tetrahydrofuran (1:1, 30 ml each)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. additionethyl acetate was added to the residue
  7. filtrationThe obtained solid was collected by filtration

出典と根拠

ORDレコード
ord-1c98debadbab4c33b5df6cb7d75d9def
出典データセット
uspto-grants-2007_05
特許番号
US07211572B2

反応ノート

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