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

HRID 931767노트

반응식

HRID 931767 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

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온도
80 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a9014c14170b44458a76b925afbb6f2b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296758B2

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