Oxalic Acid → HCID 86731689, compound

HRID 1504807Notes

Reaction equation

HRID 1504807 reaction equation
[N:1]([CH:4]([C:17]([F:20])([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:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>O1CCCC1.[Co](Cl)Cl>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[NH2:1][CH:4]([C:17]([F:18])([F:19])[F:20])[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

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 86731688Carbamic acid, N-(2-azido-3,3,3-trifluoropropyl)-, phenylmethyl ester

Product 1

HCID 86731689HCID 86731689, compound

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2-azido-3,3,3-trifluoropropyl)carbamate (107 g, 371 mmol) in tetrahydrofuran (1000 mL) was added cobalt chloride (17.8 g, 137 mmol) followed by sodium borohydride (1.0 M in water, 1.5 L, 1.5 mol) dropwise over a period of 2 hours. After 2 hours post-addition, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (3×200 mL). The organics were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. To the residue was added oxalic acid (0.37 M solution in ethyl acetate, 1.5 L, 560 mmol). After 16 hours, the reaction mixture was filtered to afford benzyl (2-amino-3,3,3-trifluoropropyl)carbamate oxalic acid salt. The material was used without further purification.

Workup

  1. additionAfter 2 hours post-addition
  2. filtrationthe reaction mixture was filtered
  3. extractionthe filtrate was extracted with ethyl acetate (3×200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-394e33c0b31d4f6a8054940a12ba8f6d
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

Loading…