Water → HCID 24862304, compound

HRID 2236120Notes

Reaction equation

HRID 2236120 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.FC(F)(F)S(O[C@H:44]1[CH2:49][CH2:48][O:47][C:45]1=[O:46])(=O)=O.O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([O:30][C@@H:44]2[CH2:49][CH2:48][O:47][C:45]2=[O:46])[CH:27]=[CH:28][CH:29]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 219497323-((Benzo[d]oxazol-2-yl(3-(4-methoxyphenoxy)propyl)amino)methyl)phenolHCID 86628935HCID 86628935, compound

Product 1

HCID 24862304HCID 24862304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In an argon atmosphere, N-(benzoxazole-2-yl)-N-(3-(4-methoxyphenoxy)propyl)-3-hydroxybenzylamine (200 mg) was dissolved in dichloromethane (1.5 mL), and triethylamine (0.11 mL) was added dropwise to the solution at room temperature, followed by stirring for 5 minutes at the same temperature. Subsequently, a solution of (S)-2-trifluoromethanesulfonyloxybutyrolactone (174 mg) in dichloromethane (1 mL) was added dropwise to the mixture over 10 minutes at room temperature, followed by stirring for 5 hours at the same temperature. The reaction mixture was added to water (50 mL), and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate and concentrating under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=1/1), to thereby yield a colorless oil (242 mg, 100′, 98.1% ee).

Workup

  1. stirringby stirring for 5 hours at the same temperature
  2. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  3. washwashed with saturated brine
  4. dry with materialby drying over sodium sulfate anhydrate
  5. concentrationconcentrating under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  7. customto thereby yield a colorless oil (242 mg, 100′, 98.1% ee)

Sources & evidence

ORD record
ord-5d27043f2c344e2eb6aad5232c42fe3f
Source dataset
uspto-grants-2010_05
Patent number
US07714141B2

Reaction notes

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