Triethylamine → HCID 59830084, compound

HRID 1095439Notes

Reaction equation

HRID 1095439 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C[C:9]([CH3:14])(C)[C:10]([Cl:12])=O.[Li]CCCC.[CH2:20]([C@H:27]1[CH2:31][O:30][C:29](=[O:32])[NH:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[O:33]1[CH2:37][CH2:36]NC1=O>O1CCCC1>[CH2:20]([C@H:27]1[CH2:31][O:30][C:29](=[O:32])[N:28]1[C:37](=[O:33])/[CH:36]=[CH:7]/[C:6]1[CH:14]=[CH:9][C:10]([Cl:12])=[CH:4][N:3]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 59830084HCID 59830084, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of the acid from preparation 4 (2.44 g, 8.2 mmol) in tetrahydrofuran (15 mL) was cooled to −78° C. under nitrogen. Triethylamine (2.85 mL, 20 mmol) was added dropwise followed by trimethylacetyl chloride (1.11 mL, 9.0 mmol), controlling the rate of addition so that the temperature stayed below −65° C. The mixture was then stirred at −78° C. for 2 hours. nBuLi (2.5 M in hexanes, 4.26 mL, 10.7 mmol) was added dropwise to a solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (1.74 g, 9.8 mmol) in tetrahydrofuran (15 mL) under nitrogen at −78° C., controlling the rate of addition so that the temperature stayed below −65° C. After stirring at −78° C. for 20 minutes the solution of oxazolidinone anion was added via cannula to the mixed anhydride solution at −78° C. The reaction mixture was stirred at −78° C. for 20 minutes then allowed to warm slowly to room temperature overnight. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (30 mL) and then concentrated in vacuo to remove the tetrahydrofuran. The solid precipitate was filtered and washed with diethyl ether to give the title compound (1.52 g, 54%) as a buff solid. The ether washings were evaporated to dryness, slurried in diethyl ether and filtered to give further product (0.42 g, 15%). 1H NMR (CDCl3, 400 MHz) δ 2.84 (1H, t), 3.37 (1H, d), 4.22 (2H, m), 4.78 (1H, m), 7.2-7.4 (5H, m), 7.51 (1H, d), 7.69 (1H, d), 7.86 (1H, d), 8.23 (1H, d), 8.62 (1H, s); LRMS (APCI+) 343 [MH+].

Workup

  1. additionthe rate of addition so that the temperature
  2. customstayed below −65° C
  3. additionthe rate of addition so that the temperature
  4. customstayed below −65° C
  5. stirringThe reaction mixture was stirred at −78° C. for 20 minutes
  6. temperatureto warm slowly to room temperature overnight
  7. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (30 mL)
  8. concentrationconcentrated in vacuo
  9. customto remove the tetrahydrofuran
  10. filtrationThe solid precipitate was filtered
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-bab5a512195341829b599b619fd6d8ab
Source dataset
uspto-grants-2012_03
Patent number
US08138188B2

Reaction notes

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