Acetic Acid → HCID 59854982, compound

HRID 2375465Notes

Reaction equation

HRID 2375465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([C@H:18]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]2[F:24])[CH3:17])=[O:15])[C@:11]([CH2:31][OH:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]=1.C(O)(=O)C.[CH3:37][C:38]([CH3:40])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([C@H:18]2[CH2:23][CH2:22][N:21]([CH:38]([CH3:40])[CH3:37])[CH2:20][C@H:19]2[F:24])[CH3:17])=[O:15])[C@:11]([CH2:31][OH:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 59854970HCID 59854970, compound

Product 1

HCID 59854982HCID 59854982, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 38 mg (0.085 mmol) of 10-2 in 1 mL of 1,2-dichloroethane was added 20 μL (0.34 mmol) of acetic acid, 25 μL (0.34 mmol) of acetone, and 27 mg (0.13 mmol) of Na(OAc)3BH. After stirring overnight, the reaction was partitioned between EtOAc and saturated aqueous NaHCO3, the organic phase was washed again with NaHCO3, H2O, brine, dried over Na2SO4, and concentrated by rotary evaporation. The residue was purified by reverse phase chromatography with 95:5 to 5:95 H2O/CH3CN (both with 0.1% TFA). The fractions were basified with NaHCO3 to provide 11-1 as a colorless film. Data for 11-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.3 (s, 1H), 5.3 (m, 1H), 4.95-4.8 (m, 2H), 4.6 (m, 1H), 4.45 (m, 1H), 4.1-4.0 (m, 2H), 3.2 (m, 1H), 3.15 (s, 3H), 3.0 (m, 1H), 2.8 (m, 1H), 2.45-2.25 (m, 3H), 1.75 (m, 1H), 1.1-1.0 (m, 6H) ppm. HRMS (ES) calc'd M+H for C27H32F3N3O2: 488.2519. Found: 488.2517.

Workup

  1. customthe reaction was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washthe organic phase was washed again with NaHCO3, H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by reverse phase chromatography with 95:5 to 5:95 H2O/CH3CN (both with 0.1% TFA)
  6. customto provide 11-1 as a colorless film

Sources & evidence

ORD record
ord-d9403ad5d0e942a89b8423c4320350dd
Source dataset
uspto-grants-2008_12
Patent number
US07465746B2

Reaction notes

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