Pyridine → Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate

HRID 58898Notes

Reaction equation

HRID 58898 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](O)([C:18]([F:21])([F:20])[F:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.N1C=CC=CC=1>C(OCC)C>[CH2:1]([O:8][C:9]([N:11]=[C:12]([C:18]([F:19])([F:21])[F:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 14377410Ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoro-2-hydroxypropanoate

Product 1

HCID 2758803Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoateYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoro-2-hydroxypropanoate (49.0 g, 153 mmol) in diethyl ether (350 mL) was added dropwise TFAA (35.3 g, 168 mmol) at 0° C. followed by addition of pyridine dropwise (26.5 g, 336 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 6 h. The mixture was filtered and the filtrate was concentrated to afford ethyl 2-(benzyloxycarbonylimino)-3,3,3-trifluoropropanoate (45.0 g, 97% yield), which was used directly without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3e9a425bc07c4af08a6df5b2c05bddea
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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