Pyridine → HCID 5706450, compound

HRID 878401Notes

Reaction equation

HRID 878401 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@:12](O)([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13]([F:16])([F:15])[F:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>C(OCC)C>[CH2:1]([O:8][C:9](/[N:11]=[C:12](/[C:13]([F:14])([F:16])[F:15])\[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 69402574HCID 69402574, compound

Product 1

HCID 5706450HCID 5706450, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl N-[(benzyloxy)carbonyl]-3,3,3-trifluoro-2-hydroxyalaninate (2690 g, 8.39 mol) in diethyl ether (18 L) under an atmosphere of nitrogen was added dropwise 2,2,2-trifluoroacetyl 2,2,2-trifluoroacetate (1937 g, 9.22 mol) at 0° C. followed by the addition of pyridine dropwise (1457 g, 18.44 mol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 6 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford ethyl (2E)-2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-adedade20fdd42ac842fd194f739c1fa
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

Loading…