Imidazole → (R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

HRID 1161221Notes

Reaction equation

HRID 1161221 reaction equation
[OH:1][CH2:2][C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([O:6][CH3:7])=[O:5].C(Cl)Cl.N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>>[Si:30]([O:1][CH2:2][C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([O:6][CH3:7])=[O:5])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 67088204(R)-Methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

Product 1

HCID 67088016(R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

Procedure

A round bottom flask was charged with (R)-methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate (4 g, 0.01 mol), methylene chloride (40 mL, 0.5 mol) and 1H-imidazole (1.6 g, 0.023 mol) and tert-butyldimethylsilyl chloride (2.3 g, 0.015 mol) were added at 0° C. and the reaction allowed to warm to room temperature and stirred for 16 h. The reaction mixture was quenched with water and extracted with methylene chloride. Solvent was removed under reduced pressure to recover the pure product as an orange solid. MS m/z=407.5 (M+H).

Workup

  1. additionwere added at 0° C.
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. customSolvent was removed under reduced pressure
  5. customto recover the pure product as an orange solid

Sources & evidence

ORD record
ord-2b22a4baf2484b9a9c28bb75f49e554a
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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