2-[3-(Trifluoromethyl)phenyl]oxirane → HCID 86740750, compound

HRID 1381272Notes

Reaction equation

HRID 1381272 reaction equation
[NH2:1][CH:2]([CH3:17])[CH2:3][C:4]1[S:8][C:7](/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]2[O:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1>CS(C)=O>[OH:28][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=1)[CH2:27][N:1]([CH2:27][CH:26]([OH:28])[C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:30])([F:29])[F:18])[CH:21]=1)[CH:2]([CH3:17])[CH2:3][C:4]1[S:8][C:7](/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 139032662-[3-(Trifluoromethyl)phenyl]oxirane2×HCID 86740751HCID 86740751, compound

Product 1

HCID 86740750HCID 86740750, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5 g of ethyl (E)-5-[(RS)-2-aminopropyl]-β-methyl-2-thiopheneacrylate and 3.7 g of m-(trifluoromethyl)phenylethylene oxide were stirred at 90° for 22 hours in 50 ml of dimethyl sulphoxide. A further 1.23 g of m-(trifluoromethyl)phenylethylene oxide were added and the mixture was heated to 90° for a further 19 hours. The working-up was carried out in analogy to Example 4. Chromatography on silica gel gave ethyl (E)-5-[(RS)-2-[bis-[(RS)-β-hydroxy-m-(trifluoromethyl)phenethyl]amino]propyl]-β-methyl-2-thiopheneacrylate; ε323 =17310.

Workup

  1. temperaturethe mixture was heated to 90° for a further 19 hours

Sources & evidence

ORD record
ord-103bef7fcfc746d188e506e212ed1f37
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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