1,2-Dichloroethane → (R)-allyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate

HRID 1365520Notes

Reaction equation

HRID 1365520 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[CH:18]=2)([NH2:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.ClCCCl.C(=O)([O-])[O-].[K+].[K+].[C:38](Cl)(=[O:43])[O:39][CH2:40][CH:41]=[CH2:42]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([NH:16][C:38](=[O:43])[O:39][CH2:40][CH:41]=[CH2:42])([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:20]=[C:19]([F:27])[CH:18]=2)[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 18052Allyl chloroformateHCID 58919949(R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine

Product 1

HCID 58920517(R)-allyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate

Procedure

(R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine was dissolved in DCE (400 uL, 0.1 M in DCE, 40 umol) and potassium carbonate added (100 mg, 723 umol, 18 eq), followed by allyl carbonochloridate (400 uL, 0.2 M in DCE, 80 umol, 2.0 eq). The reaction mixture was agitated at room temperature for 18 h and then filtered and rinsed with DCE (2×250 uL). The combined filtrate was evaporated and the residue was redissolved in 1 mL of MeOH and purified by reverse phase preparative HPLC using MeOH:water:TFA system. (R)-allyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate was obtained as a colorless oil (13.2 umol, 33% yield). LCMS: M+calc=478.11; found=479.35.

Workup

  1. filtrationfiltered
  2. washrinsed with DCE (2×250 uL)
  3. customThe combined filtrate was evaporated
  4. dissolutionthe residue was redissolved in 1 mL of MeOH
  5. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-564bb53e1af649b99fcaf5f00dbfe61d
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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