Triethylamine → HCID 58116472, compound

HRID 661240Notes

Reaction equation

HRID 661240 reaction equation
C(OC1N=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][N:11]([C:26](OC3C=CC([N+]([O-])=O)=CC=3)=[O:27])[CH2:10]2)[O:6]N=1)C.[CH2:38](N(CC)CC)C.Cl[C:46](OC1C=CC([N+]([O-])=O)=CC=1)=[O:47]>C(O)(=O)C.[Pd].[Pt](=O)=O>[C:26]([N:11]1[CH2:12][CH:13]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][C:22]([F:23])([F:25])[F:24])=[CH:19][CH:20]=2)[CH2:14][CH:9]([C:7]([O:47][CH3:46])=[O:6])[CH2:10]1)(=[O:27])[CH3:38]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116539HCID 58116539, compound

Product 1

HCID 58116472HCID 58116472, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7.00 g (23.4 mmol) of the compound from Example 62A in concentrated acetic acid (150 ml) was admixed with 3.00 g of palladium/carbon (10% palladium) and 5.50 g of platinum(IV) oxide and then hydrogenated under a hydrogen atmosphere at standard pressure until conversion is complete. The reaction solution was filtered through Celite, the filter residue was washed with methanol/water and the combined filtrates were concentrated under reduced pressure. The residue (10.5 g) was taken up in dichloromethane (315 ml) and then admixed with 18.2 ml (13.2 g, 131 mmol) of triethylamine, and then admixed at 0° C. with 5.86 g (29.1 mmol) of 4-nitrophenyl chloroformate. The mixture was stirred at 0° C. for 2 h, then warmed to RT and stirred overnight. The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of preparative HPLC and the title compound was thus obtained as a by-product. Yield: 1.32 g (14% of theory, purity 85%)

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe filter residue was washed with methanol/water
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. temperaturewarmed to RT
  5. stirringstirred overnight
  6. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  7. dry with materialthe organic phase was dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-3c93715f2c284c2a97d49a1a28d53139
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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