Nitromethane → HCID 86586176, compound

HRID 429387Notes

Reaction equation

HRID 429387 reaction equation
CC([O-])(C)C.[K+].[N+:7]([CH3:10])([O-:9])=[O:8].[O:11]=[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH:22]([C:35](=[O:37])C)[CH:23]([NH:31][C:32]([CH3:34])=[O:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C)C=O>[O:11]=[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH:22]([CH:35]([OH:37])[CH2:10][N+:7]([O-:9])=[O:8])[CH:23]([NH:31][C:32]([CH3:34])=[O:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 23665647Potassium tert-butoxideHCID 86586177HCID 86586177, compound

Product 1

HCID 86586176HCID 86586176, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.15 g (10.0 mMol) of KOtBu (potassium tertbutoxide) in dimethylformamide (30 mL) at 0° C. under nitrogen and nitromethane (1.75 mL, 32.5 mMol) was added 3-(1,2,3,4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-4-oxo-pentanoic acid, tert-butyl ester (3.6 g, 10.0 mMol). After 3 hours at 0° C. the reaction was quenched by addition of 1.5 mL of acetic acid and partitioned between ethyl acetate (200 mL) and water (20 mL). The organic phase was washed with saturated aqueous sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated under reduced pressure. Purification of the residue over silica (elution with dichloromethane/methanol 20:1) gave 2.7 g of 3-(1, 2, 3, 4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-4-hydroxy-5-nitro-pentanoic acid, tert-butyl ester as 1:1 mixture of diastereomers.

Workup

  1. customAfter 3 hours at 0° C. the reaction was quenched by addition of 1.5 mL of acetic acid
  2. custompartitioned between ethyl acetate (200 mL) and water (20 mL)
  3. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue over silica (elution with dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-0152d58a807d428da081492917fa845d
Source dataset
uspto-grants-2001_11
Patent number
US06316415B1

Reaction notes

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