Oxalic Acid → HCID 86731695, compound

HRID 1504810Notes

Reaction equation

HRID 1504810 reaction equation
[N:1]([CH:4]([CH:17]([F:19])[F:18])[CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[N+]=[N-].[BH4-].[Na+].[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>C1COCC1.[Co](Cl)Cl>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[NH2:1][CH:4]([CH:17]([F:18])[F:19])[CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 86731694HCID 86731694, compound

Product 1

HCID 86731695HCID 86731695, compound

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2-azido-3,3-difluoropropyl)carbamate (305 g, 1.13 mol) (1500 mL) and cobalt chloride (60 g, 460 mmol) in THF was added dropwise sodium borohydride (2.44 M solution in water, 2000 mL, 4.87 mol) over a period of 2 hours. After 2 hours, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (2×2000 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and diluted with oxalic acid (1.22 M solution in ethyl acetate, 1500 mL, 1.83 mol). After 2 hours, the mixture was filtered to afford benzyl (2-amino-3,3-difluoropropyl)carbamate oxalic acid salt. The material was used without further purification.

Workup

  1. filtrationthe reaction mixture was filtered
  2. extractionthe filtrate was extracted with ethyl acetate (2×2000 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. waitAfter 2 hours
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-d2b9e440dc0b442b85c562f7eed3e4d5
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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