Water → HCID 69044148, compound

HRID 884384Notes

Reaction equation

HRID 884384 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH:11]=[CH2:12])[N:7]1C(OC(C)(C)C)=O)=[O:5])[CH3:2].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C([O-])(O)=O.[Na+].O>C(Cl)Cl.CCOCC>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH:11]=[CH2:12])[NH:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 68260485HCID 68260485, compound

Product 1

HCID 69044148HCID 69044148, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

130 mg of 172 (0.46 mmol) was dissolved in 3 ml of anhydrous CH2Cl2, cooled to 0° C. and added dropwise with 90 ml of TMSOTf (0.466 mmol, 1.01 eq.). After 15 min, this was added with 0.5 ml of saturated NaHCO3 solution, 0.5 ml of H2O and 10 ml of Et2O, and the batch was allowed to come to RT. Following phase separation, the organic phase was dried over MgSO4, filtered and concentrated. The resulting crude product was purified using silica gel column chromatography (DCM/MeOH 25:1) to isolate 54 mg of amine 174 (0.32 mmol, 70%) as a slightly yellowish oil (mixture of diastereomers, cis/trans=4:1).

Workup

  1. customto come to RT
  2. customFollowing phase separation
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-26d9ea4e31fe4b06b7d70b3b05b2419a
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

Loading…