Carbon Dioxide → HCID 67458593, compound

HRID 1519233Notes

Reaction equation

HRID 1519233 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:5][C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[Li]CCCC.[C:26](=[O:28])=[O:27]>C1COCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:6]2[O:5][C:4]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:3][C:2]=2[C:26]([OH:28])=[O:27])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 67451842HCID 67451842, compoundHCID 178418339Butyllithium

Product 1

HCID 67458593HCID 67458593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a dry flask was added 4-bromo-5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (50 mg, 0.133 mmol) and THF (2669 μl), and the reaction mixture was cooled to −78° C. nBuLi (92 μl, 0.147 mmol) was added slowly and the reaction mixture was stirred at −78° C. for 30 min. Crushed dry ice was added, the reaction mixture was stirred at −78° C. for 20 min, quenched with 10% KHSO4, and allowed to warm to RT. The reaction mixture was extracted with EtOAc, dried over sodium sulfate and concentrated in vacuo to give 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxylic acid (47 mg crude) to be used as is in the next step. MS: M+H=340.

Workup

  1. additionwas added slowly
  2. stirringthe reaction mixture was stirred at −78° C. for 20 min
  3. customquenched with 10% KHSO4
  4. temperatureto warm to RT
  5. extractionThe reaction mixture was extracted with EtOAc
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e59bc2d56a144115aba3a2fbe2222835
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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