Diethyl Ether → HCID 86670011, compound

HRID 920533Notes

Reaction equation

HRID 920533 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][C:5]=1[C:15]([F:18])([F:17])[F:16].CCOCC.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([NH:31][CH2:3][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][C:5]=1[C:15]([F:18])([F:17])[F:16])[OH:1])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7504BenzylamineHCID 86670009HCID 86670009, compound

Product 1

HCID 86670011HCID 86670011, compound

Conditions

Temperature
80 °C

Procedure

Methanesulfonic acid 4-oxiranyl-3-trifluoromethyl-phenyl ester (23.54 g; 79.2 mmol) was dissolved in benzylamine (26 mL). The resulting mixture was stirred at 80° C. for 4 h. After cooling to RT, Et2O was added and the mixture cooled to 0° C. The formed precipitate was collected by filtration, washed with Et2O, and dried under vacuum, at 40° C., to afford methanesulfonic acid 4-(2-benzylamino-1-hydroxy-ethyl)-3-trifluoromethyl-phenyl ester as a white solid (26.87 g) which was used as such.

Workup

  1. temperatureAfter cooling to RT
  2. temperaturethe mixture cooled to 0° C
  3. filtrationThe formed precipitate was collected by filtration
  4. washwashed with Et2O
  5. customdried under vacuum, at 40° C.

Sources & evidence

ORD record
ord-d80a0df16eeb412f85b24041f77e82a7
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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