Acetic Anhydride → (S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

HRID 931767ノート

反応式

HRID 931767 の反応式
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C@@H:13]([C:19]1[C:20]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[C:21]2[C:26](=[CH:27][C:28]=1[CH3:29])[N+:25]([O-])=[C:24]([CH3:31])[CH:23]=[CH:22]2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH3:11])([CH3:10])[CH3:9].C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(C)C=C2)C(OCC)=O)(C)(C)C>>[C:1]([O:4][CH2:31][C:24]1[CH:23]=[CH:22][C:21]2[C:26](=[CH:27][C:28]([CH3:29])=[C:19]([C@H:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:20]=2[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[N:25]=1)(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 66631334(S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxideHCID 68587086(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)acetate

生成物 1

HCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

反応条件

温度
80 °C

実験手順

Acetic anhydride was added to a flask containing (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide (compound of Example 14) (42 mg, 0.095 mmol). The mixture was stirred at 80° C. for 1 hour. Acetic anhydride was removed under vacuum. The residue was dissolved in ethyl acetate (50 mL). The organic layer was washed with NaHCO3 solution and water, dried and concentrated in vacuo. The obtained residue was used for next step reaction without purification. LCMS-ESI+ (m/z): 484.2, 486.2 (M+H)+.

後処理

  1. customAcetic anhydride was removed under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washThe organic layer was washed with NaHCO3 solution and water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was used for next step reaction without purification

出典と根拠

ORDレコード
ord-a9014c14170b44458a76b925afbb6f2b
出典データセット
uspto-grants-2016_03
特許番号
US09296758B2

反応ノート

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