Triethylamine → HCID 86690947, compound

HRID 714740Notes

Reaction equation

HRID 714740 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[C:11]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[CH:10]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.O>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:21]2[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:29])([F:28])[F:30])[C:23](=[O:24])[N:19]([CH2:18][C:11]3[CH:10]=[C:9]([C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=4[Cl:1])[CH:14]=[CH:13][C:12]=3[CH2:15][OH:16])[N:20]=2)=[CH:33][CH:34]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86690946HCID 86690946, compound

Product 1

HCID 86690947HCID 86690947, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

230 mg (0.39 mmol) of the compound from Example 134 were dissolved in 5 ml of THF, the solution was cooled to 0° C. and 55 μl (0.39 mmol) of triethylamine and also 56 μl (0.43 mmol) of isobutyl chloroformate were added. The mixture was stirred at 0° C. for 1 h. The suspension was then filtered through a Seitz frit into a flask cooled to 0° C., and the residue was rinsed with about 2 ml of THF. With vigorous stirring, this solution was added to a solution, cooled to 0° C., of 44 mg (1.18 mmol) of sodium borohydride in 0.6 ml of water. After 1 h, 5 ml of saturated aqueous sodium bicarbonate solution were added, and the mixture was warmed to RT. The mixture was extracted with 15 ml of ethyl acetate. The organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying over sodium sulfate, the mixture was filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 13 mg (6% of theory) of the target compound.

Workup

  1. filtrationThe suspension was then filtered through a Seitz frit into a flask
  2. temperaturecooled to 0° C.
  3. washthe residue was rinsed with about 2 ml of THF
  4. additionWith vigorous stirring, this solution was added to a solution
  5. waitAfter 1 h
  6. temperaturethe mixture was warmed to RT
  7. extractionThe mixture was extracted with 15 ml of ethyl acetate
  8. washThe organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution
  9. dry with materialAfter drying over sodium sulfate
  10. filtrationthe mixture was filtered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-c39cc8b379224fe6876f7887c2c0ac8e
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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