Oxalyl chloride → HCID 178501142, compound

HRID 2272652Notes

Reaction equation

HRID 2272652 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C(=O)(O)[O-].[Na+]>ClCCl>[S:23]1[CH:24]=[CH:25][N:26]=[C:22]1[C:11]([C@H:8]1[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]1)=[O:13]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 5884532-TrimethylsilylthiazoleHCID 178501163HCID 178501163, compound

Product 1

HCID 178501142HCID 178501142, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (500 mg, 2.69 mmol) in dichloromethane (3 mL) at 0° C. was added oxalyl chloride (0.26 mL, 2.95 mmol) dropwise. The solution was stirred at 0° C. for 30 min and then allowed to warm to room temperature and stirred for one hour. The solution was then cooled back to 0° C. and 2-(trimethylsilyl)-1,3-thiazole (0.63 mL, 4.03 mmol) was added. The solution was allowed to warm to room temperature and then stirred for one hour. The solution was then poured into cold saturated sodium bicarbonate and then diluted with dichlormethane. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes) to provide methyl trans-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate. MS ESI calc'd. for C12H16NO3S [M+H]+ 254. found 254. 1H NMR (500 MHz, CDCl3) δ 8.01 (dd, J=1.6, 2.9 Hz, 1H), 7.67 (dd, J=1.7, 2.9 Hz, 1H), 3.77-3.67 (m, 3H), 3.62 (t, J=11.1 Hz, 1H), 2.35 (t, J=10.4 Hz, 1H), 2.18-2.06 (m, 4H), 1.68-1.48 (m, 4H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for one hour
  3. temperatureThe solution was then cooled back to 0° C.
  4. temperatureto warm to room temperature
  5. stirringstirred for one hour
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d3b4a701ed624e00a6aa83b927fbe98c
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

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