Sodium Bicarbonate → HCID 53927366, compound

HRID 489053Notes

Reaction equation

HRID 489053 reaction equation
[O-]Cl=O.[Na+].[CH2:5]([O:12][C:13]([NH:15][C@H:16]([C:20]([O:22][CH2:23][C:24]1[O:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=1)=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])(O)=[O:32].[Na+]>O.CC#N>[CH2:5]([O:12][C:13]([NH:15][C@H:16]([C:20]([O:22][CH2:23][C:24]1[O:28][C:27]([C:29]([OH:32])=[O:30])=[CH:26][CH:25]=1)=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668197Sodium ChloriteHCID 53819898HCID 53819898, compound

Product 1

HCID 53927366HCID 53927366, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of NaClO2 (2.8 mmol) in 3 mL water was added dropwise to a stirred solution of 5-[(N-benzyloxycarbonyl-L-valyloxy)methyl]-2-furaldehyde (798 mg, 2.22 mmol) from step (a) in 3 mL MeCN, with cooling in an ice bath. After 2.5 h, the ice bath was removed, 2 mL more MeCN was added, and the two-phase liquid reaction mixture was stirred at room temperature for 25 h. The reaction mixture was diluted with water, made basic with saturated NaHCO3, and extracted with ethyl acetate (3×50 mL). The separated aqueous solution was acidified to pH 2 with 5% aqueous HCl and extracted with ethyl acetate (3×50 mL). This second ethyl acetate solution was washed with brine, dried over anhydrous Na2SO4, and evaporated to dryness under vacuum to give the carboxylic acid (287 mg, 34%) which was used in the next step without further purification. The compound can be activated and esterified direct to a drug or further modified as described below.

Workup

  1. temperaturewith cooling in an ice bath
  2. customthe ice bath was removed
  3. addition2 mL more MeCN was added
  4. customthe two-phase liquid reaction mixture
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. washThis second ethyl acetate solution was washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-603eca1bed0343c68f057597c64698e1
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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