Water → HCID 67288223, compound

HRID 1045328Notes

Reaction equation

HRID 1045328 reaction equation
[CH2:1]([C@:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[OH:26])=[CH:11][C:10]=1[Cl:27])[CH2:5][OH:6])[CH:2]=[CH2:3].[OH2:36]>C(OCC)(=O)C>[C:32]([O:31][C:29]([NH:28][C@@:4]([CH2:1][CH2:2][CH3:3])([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[O:26][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:36])=[CH:11][C:10]=1[Cl:27])[CH2:5][OH:6])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 962WaterHCID 67286969HCID 67286969, compound

Product 1

HCID 67288223HCID 67288223, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A palladium on activated carbon/ethylene diamine complex (100 mg) was added to a solution of the compound of Example 33 (473 mg) in ethyl acetate (9 mL) to form a first reaction solution. This first reaction solution was stirred at normal temperature for 20 hours under hydrogen purging. The first reaction solution was filtrated through Celite, and the solvent was removed by distillation. The resultant residue was dissolved in acetonitrile (9 mL). Triethylamine (145 μL) and di-tert-butoxydicarbonate (284 mg) were added to this solution to form a second reaction solution. This second reaction solution was stirred at normal temperature for 2 hours and then left to stand overnight. Then, water was added to the second reaction solution, and the second reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the target product (434 mg) as a colorless oil.

Workup

  1. customto form a first reaction solution
  2. filtrationThe first reaction solution was filtrated through Celite
  3. customthe solvent was removed by distillation
  4. dissolutionThe resultant residue was dissolved in acetonitrile (9 mL)
  5. additionTriethylamine (145 μL) and di-tert-butoxydicarbonate (284 mg) were added to this solution
  6. customto form a second reaction solution
  7. stirringThis second reaction solution was stirred at normal temperature for 2 hours
  8. waitleft
  9. waitto stand overnight
  10. extractionthe second reaction solution was extracted with ethyl acetate
  11. washThe extract was washed with water and saturated brine in that order
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe anhydrous sodium sulfate was removed by filtration
  14. customthe solvent was removed by distillation under reduced pressure
  15. customThe resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-50ee7ac0186f4118a988956a7e8ff3c9
Source dataset
uspto-grants-2013_10
Patent number
US08569270B2

Reaction notes

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