HCID 89827399, compound → HCID 117831911, compound

HRID 2207315Notes

Reaction equation

HRID 2207315 reaction equation
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[CH2:25]Cl)[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]2([CH2:14][C:15]3[C:16](=[CH:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=3)[CH2:25]2)[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 89827399HCID 89827399, compound

Product 1

HCID 117831911HCID 117831911, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 16 (50 mg, 0.126 mmol) in toluene (2 ml) was cooled to −1° C., degassed with vacuum and flushed N2. To this solution was charged a precooled (−2 to 0° C.) aqueous NaOH (1N, 1 mL) followed by charged a catalyst 18. The resulted reaction was aged at −1 to 1° C. for several hours until complete conversion. The organic layer was purified with silica gel column chromatography (0 to 10% AcOEt/hexane) to give the desired compound 17 as oil (42 mg, 92% IY, 85% ee, R or S undetermined).

Workup

  1. customdegassed with vacuum
  2. customflushed N2
  3. additionTo this solution was charged a precooled (−2 to 0° C.) aqueous NaOH (1N, 1 mL)
  4. additionby charged a catalyst 18
  5. customThe resulted reaction
  6. waitwas aged at −1 to 1° C. for several hours until complete conversion
  7. customThe organic layer was purified with silica gel column chromatography (0 to 10% AcOEt/hexane)

Sources & evidence

ORD record
ord-079cd30a6dad4bf587548907879d6bf8
Source dataset
uspto-grants-2016_06
Patent number
US09376431B2

Reaction notes

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