Butyric Acid → HCID 71257519, compound

HRID 1619462Notes

Reaction equation

HRID 1619462 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:14]=[C:15]([S:19]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[CH:5][C:4]=1[C:30]1[O:31][CH:32]=[CH:33][CH:34]=1.[C:36](O)(=[O:40])[CH2:37][CH2:38][CH3:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[CH3:1][N:2]([CH3:35])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:14]=[C:15]([S:19]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH2:26][CH2:25]3)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[CH:5][C:4]=1[C:30]1[O:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71257611HCID 71257611, compound

Product 1

HCID 71257519HCID 71257519, compoundYield 373.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution (1.5 ml) of Y516 (60 mg, 0.098 mmol) produced in Example 35 in dimethylformamide were added n-butanoic acid (butyric acid) (20 μl, 0.02 mmol), HBTU (N,N,N′,N′-tetramethyl-O— (benzotriazol-1-yl)uronium Hexafluorophosphate) (40 mg, 0.1 mmol) and DIEA (N,N-diisopropylethylamine) (30 ml, 0.18 mmol), and the mixture was stirred at room temperature for 18 hr. Then, the reaction mixture was cooled, poured into cold water, and extracted with chloroform. The obtained chloroform extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol (40:1)) to give the title compound (Y639) (44 mg, 77%).

Workup

  1. temperatureThen, the reaction mixture was cooled
  2. extractionextracted with chloroform
  3. extractionThe obtained chloroform extract
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol (40:1))

Sources & evidence

ORD record
ord-e9bec58091e244ce95bd5cd1f800302c
Source dataset
uspto-grants-2014_07
Patent number
US08772297B2

Reaction notes

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