Water → Tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

HRID 1853831Notes

Reaction equation

HRID 1853831 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[S:13][CH:14]=[CH:15][C:5]=3[C:4]=2[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:18][CH:17]=1.[H-].[Na+].Cl[C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36].O>C1COCC1>[CH:38]([O:37][C:35]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[S:13][CH:14]=[CH:15][C:5]=3[C:4]=2[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:18][CH:17]=1)=[O:36])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 24758Sodium hydrideHCID 67459021Tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Product 1

HCID 67457829Tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (44 mg, 0.10 mmol) in THF (2 mL) at 0° C. was added NaH (60%, 6 mg, 0.15 mmol) and the reaction was stirred at that temperature for 1 h. Isopropyl chloroformate (21 μL, 0.15 mmol) was added and the resulting mixture was stirred at rt for 3 h. Water was added and the mixture was extracted with dichloromethane (2×15 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (26 mg, 50%) as a solid: ESI MS m/z 523 [C28H30N2O6S+H]+.

Workup

  1. stirringthe resulting mixture was stirred at rt for 3 h
  2. extractionthe mixture was extracted with dichloromethane (2×15 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-922ff507a4054c6f9f931d4c280cef8e
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

Loading…