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

HRID 931767Notes

Reaction equation

HRID 931767 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Conditions

Temperature
80 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-a9014c14170b44458a76b925afbb6f2b
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

Loading…