Acetic Anhydride → HCID 68911310, compound

HRID 887665Notes

Reaction equation

HRID 887665 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].CCN(CC)CC.[CH3:28][C:29](OC(C)=O)=[O:30]>C(Cl)Cl>[C:29]([N:17]1[CH2:18][CH2:19][CH2:20][C@@H:16]1[CH2:15][O:14][C:6]1[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:30])[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68530622HCID 68530622, compound

Product 1

HCID 68911310HCID 68911310, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(((3-nitro-5-(trifluoromethyl)phenyl)oxy)methyl)pyrrolidine (3.46 g, 11.9 mmols, 1 eq) was dissolved in 100 mL of CH2Cl2. Et3N (5 mL, 35.7 mmols, 3 eq) was added followed by Ac2O (1.2 mL, 13.1 mmols, 1.1 eq). The reaction was stirred at RT for 1.5 h. The solvent was removed in vacuo and the residue dissolved in EtOAc. The solution was washed once each with saturated NH4Cl, 1 N HCl, and twice with brine. The organic layer was dried over Na2SO4 filtered and concentrated in vacuo. The crude material was purified on a Biotage chromatography system eluting with a gradient of 10% to 75% EtOAc:hexane to yield the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe solution was washed once each with saturated NH4Cl, 1 N HCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified on a Biotage chromatography system
  8. washeluting with a gradient of 10% to 75% EtOAc

Sources & evidence

ORD record
ord-ef88485251c3498eb9d033ee5318827b
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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