Sodium Bicarbonate → HCID 59783585, compound

HRID 718032Notes

Reaction equation

HRID 718032 reaction equation
[CH:1]1[C:6]2[C:7]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[C:29](=O)(O)[O-].[Na+]>C(O)=O.O>[CH3:29][N:8]1[CH:7]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=2)[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]1=2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59783546HCID 59783546, compound

Product 1

HCID 59783585HCID 59783585, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

Title compound 4 (0.508 g, 1.48 mmol) was dissolved in formic acid (5.0 mL) and the mixture was cooled at 4° C. Sodium borohydride (0.502 g) was added and the reaction mixture was stirred at room temperature for 90 min. The mixture was diluted in water (50 mL) and solid sodium bicarbonate was added until alkaline (pH=8-9). This mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over sodium sulfate and evaporated. The crude was purified by flash chromatography with 10% ethyl acetate in hexanes to afford title compound 7 (408 mg, 77%) as a colorless oil. LRMS (ESI): (calc) 359.15. (found) 360.3 (MH)+.

Workup

  1. extractionThis mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude was purified by flash chromatography with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7c15cb4e4d3a4467bc2b20f360920995
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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