Triethylamine → HCID 89676984, compound

HRID 2207054Notes

Reaction equation

HRID 2207054 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:28])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH2:26][OH:27])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:28])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH:26]=[O:27])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 89676667HCID 89676667, compound

Product 1

HCID 89676984HCID 89676984, compound

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

To a solution of (S)-2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate (180 mg, 0.4 mmol) in DCM/DMSO (0.5 ml/0.5 ml) at 0° C. was added triethylamine (192 μl), followed by SO3-pyridine (222 mg). The mixture was stirred for 1 hour, and was quenched with ice-water. The water phase was extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate solution, water and brine, and was dried over sodium sulfate. Concentration gave (S)-2-(5-bromo-2-formyl-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate. ESI+ (m/z): [M+H]+ calc'd for C22H29BrNO4: 450.1; Found: 450.2.

Workup

  1. customwas quenched with ice-water
  2. extractionThe water phase was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated sodium bicarbonate solution, water and brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-c2b46df7254f478aade545d671858984
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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