Ethyl Acetate → HCID 58975065, compound

HRID 737064Notes

Reaction equation

HRID 737064 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:34]=[CH:33][C:21]([C:22]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:23])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH3-]C#N.[Na+].CCOC(C)=O>C(O)(C(F)(F)F)=O.O>[CH:1]1([CH:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:23])=[CH:33][CH:34]=3)(=[O:16])=[O:17])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydride2×HCID 11225304HCID 11225304, compound

Product 1

HCID 58975065HCID 58975065, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
2.5 °C

Procedure

Add 4-(3-cyclopentyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide (0.152 g, 0.319 mmol) portionwise to a stirring mixture of NaCNBH3 (0.096 g, 1.52 mmol) in TFA at 0 to 5° C. under N2. Stir the mixture for 15 minutes at 0-5° C., allow to warm to ambient temperature and add an additional 0.096 g NaCNBH3. Stir the resulting yellow solution for 2 h at ambient temperature, dilute with H2O (13.0 mL) and stir overnight. Pour the reaction mixture is into EtOAc (100 mL). Separate the EtOAc, extract with H2O, 5% NaHCO3 and wash with brine. Separate the EtOAc, dry (MgSO4), filter and evaporate giving a glass. Chromatograph on the chromatotron eluting with EtOAc-hexane 3:7 to give 0.060 g of the title compound: Mass spectrum (m/e) (M+H) 479.1805; found 479.1788.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringStir the resulting yellow solution for 2 h at ambient temperature
  3. stirringstir overnight
  4. additionPour the reaction mixture
  5. customSeparate the EtOAc
  6. extractionextract with H2O, 5% NaHCO3
  7. washwash with brine
  8. customSeparate the EtOAc
  9. dry with materialdry (MgSO4)
  10. filtrationfilter
  11. customevaporate
  12. customgiving a glass
  13. washChromatograph on the chromatotron eluting with EtOAc-hexane 3:7

Sources & evidence

ORD record
ord-274d99bdcffd4348bd15633ce6242a2b
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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