Sodium borohydride → HCID 18512377, compound

HRID 1370805Notes

Reaction equation

HRID 1370805 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH:30]([OH:33])CO)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[BH4-].[Na+]>C1C=CC=CC=1.C(O)C.C(OCC)C>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:33])=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 18512114HCID 18512114, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 18512377HCID 18512377, compoundYield 9.8%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

The product from Example 41A (0.6 g, 1.27 mmoles) in benzene (11.6 mL) and ethanol (11.6 mL) was treated with lead tetraacetate (0.6215 g, 1.4 mmoles) at 0° C. The reaction mixture turned from clear and colorless to light yellow and was stirred for 15 minutes. The mixture was diluted with diethyl ether (100 mL), filtered through a 1 inch pad of 1:1 Celite:silica gel and the filtrate was concentrated under reduced pressure. The residue (0.07 g, 0.16 mmoles) was dissolved in ethanol (1.0 mL) and treated with sodium borohydride (0.006 g, 0.16 mmoles). After 30 minutes, the reaction mixture was filtered through silica gel using 2:1 ethyl acetate:hexanes and concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column to provide the title compound as a brown oil (0.055 g). 1H NMR (300 MHz, CDCl3) δ7.21 (m, 10H), 6.75 (dd, J=8.8, 1.7 Hz, 2H), 6.04 (s, 1H), 4.66 (dd, J=5.4, 3.7 Hz, 1H), 4.57 (d, J=10.3 Hz, 2H), 4.52 (d, J=10.3 Hz, 2H), 4.21 (s, 1H), 4.02 (m, 1H), 3.95 (m, 1H), 3.72 (s, 1H), 2.76 (s, 3H), 1.98 (s, 3H); MS (APCI+) m/z 441 (M+H)+.

Workup

  1. filtrationfiltered through a 1 inch pad of 1:1 Celite
  2. concentrationsilica gel and the filtrate was concentrated under reduced pressure
  3. waitAfter 30 minutes
  4. filtrationthe reaction mixture was filtered through silica gel using 2:1 ethyl acetate
  5. concentrationhexanes and concentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-99f798c41123473db550e771309def16
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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