2,3-Dihydroxybutanedioic Acid → HCID 13891198, compound

HRID 973925Notes

Reaction equation

HRID 973925 reaction equation
C([O:3][C:4](=[O:23])[C:5]([F:22])([F:21])[C@H:6]([OH:20])[C@H:7]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C.[OH-].[Na+].C(O)(=O)C(C(C(O)=O)O)O>CO.O>[C:9]([NH:8][C@H:7]([C@H:6]([C:5]([F:21])([F:22])[C:4](=[O:3])[OH:23])[OH:20])[CH2:16][CH:17]([CH3:19])[CH3:18])([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 14798Sodium HydroxideHCID 13893282Ethyl (3R,4S)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-difluoro-3-hydroxy-6-methylheptanoate

Product 1

HCID 13891198HCID 13891198, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1 g N--BOC--(4S,3R)-2,2-difluorostatine ethyl ester is dissolved in methanol/water and reacted with 0.25 g of concentrated aqueous sodium hydroxide. After 2 hours the mixture is made acidic with 2N tartaric acid solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. N--BOC--(4S,3R)-2,2-difluorostatine is obtained (crude).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b9c92a757000415a93138fafc09cebff
Source dataset
uspto-grants-1991_11
Patent number
US05066643

Reaction notes

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