Tetrahydrofuran → HCID 57733409, compound

HRID 1920753Notes

Reaction equation

HRID 1920753 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[N:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14]=2[CH3:33])=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1>[Zn]>[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[C:18]([NH2:23])[CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[N:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14]=2[CH3:33])=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57733337HCID 57733337, compound

Product 1

HCID 57733409HCID 57733409, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a stirred solution of 3-methyl-8-nitro-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (1am, 10 mg, 0.023 mmol) in tetrahydrofurane (0.15 ml) 2M aq. HCl (0.12 ml, 0.25 mmol) and Zn powder (45 mg, 0.69 mmol) was added. After 30 min the mixture was filtered and partitioned between ethyl acetate (4 ml) and sat. aq. NaHCO3 (2 ml), then brine (3 ml). The organic solution was dried (MgSO4) and evaporated to afford 5.9 mg of the title compound (70% yield). LC-MS (m/z) 412.4 (MH+); tR=1.37.

Workup

  1. filtrationAfter 30 min the mixture was filtered
  2. custompartitioned between ethyl acetate (4 ml) and sat. aq. NaHCO3 (2 ml)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0ac7d0700b42400d8eb7710bda208b23
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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