Acetic Acid → HCID 11518665, compound

HRID 2092180Notes

Reaction equation

HRID 2092180 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][NH:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[N:19][N:20]2[C:25]([O:27][CH3:28])=[O:26])=[O:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:43]1([CH2:49][CH:50]=O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(O)(=O)C>ClC(Cl)C>[C:43]1([CH2:49][CH2:50][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH:2]2[CH2:11][NH:12][C:13]([NH:15][C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH:18]=[N:19][N:20]3[C:25]([O:27][CH3:28])=[O:26])=[O:14])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67236666HCID 67236666, compound

Product 1

HCID 11518665HCID 11518665, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The product from Example 22B (0.2486 g, 0.50 mmol) and sodium triacetoxy borohydride (0.2235 g, 1.05 mmol) were suspended in dichloroethane (10 mL). The reaction flask was equipped with stir bar and spetum, then flushed with N2. Phenylacetaldehyde (0.10 mL, 0.85 mmol) was added followed by glacial acetic acid (0.2 mL, 3.4 mmol). After 1 hour of stirring at ambient temperature, the reaction mixture was quenched with water (20 mL) then partitioned between ethyl acetate/water. The aqueous phase was extracted with ethyl acetate (2×15 mL). The combined organic fractions were washed sequentially with aqueous saturated NaHCO3 (1×25 mL), water (1×25 mL), and brine (1×25 mL), dried (MgSO4), filtered and concentrated in vaco. The crude material was purified via column chromatography (2% to 5% methanol/dichloromethane) to afford the titled compound (0.1913 g, 79%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.99 (s, 1 H) 8.43 (s, 1 H) 7.80 (d, J=7.80 Hz, 1 H) 7.69 (d, J=8.48 Hz, 1 H) 7.48 (t, J=8.14 Hz, 1 H) 7.25 (m, 5 H) 7.04 (m, 1 H) 6.95 (d, J=7.46 Hz, 1 H) 6.71 (d, J=8.14 Hz, 1 H) 6.51 (t, J=6.95 Hz, 2 H) 4.03 (s, 3 H) 3.72 (m, 1 H) 3.37 (m, 3 H) 3.13 (m, 1 H) 2.82 (m, 3 H) 2.59 (m, 1 H) 1.89 (m, 1 H) 1.55 (m, 1 H). MS (ESI) m/z 484 (M+H)+, 482 (M−H)−.

Workup

  1. customThe reaction flask was equipped
  2. customspetum, then flushed with N2
  3. stirringAfter 1 hour of stirring at ambient temperature
  4. customthe reaction mixture was quenched with water (20 mL)
  5. customthen partitioned between ethyl acetate/water
  6. extractionThe aqueous phase was extracted with ethyl acetate (2×15 mL)
  7. washThe combined organic fractions were washed sequentially with aqueous saturated NaHCO3 (1×25 mL), water (1×25 mL), and brine (1×25 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vaco
  11. customThe crude material was purified via column chromatography (2% to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5d229cd74dbe4070822b0ed3c1d814b7
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

Loading…