Triethylamine → HCID 49853919, compound

HRID 1400038Notes

Reaction equation

HRID 1400038 reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:23]=[C:14]1[N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:1]34[CH2:6][CH:5]3[CH2:4][N:3]([CH2:30][C:26]3[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=3)[CH2:2]4)=[CH:12][CH:11]=2)[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67515007HCID 67515007, compound2×

Product 1

HCID 49853919HCID 49853919, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (210 mg, 0.6 mmol), in dichloroethane (25 mL), were added 3-pyridinecarboxaldehyde (0.06 mL, 0.6 mmol), triethyl amine (0.17 mL, 1.2 mmol) and sodium triacetoxyborohydride (254 mg, 1.2 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was quenched by adding saturated aq. NaHCO3 solution (20 mL) and product was extracted with DCM (3×25 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.5:9.5 MeOH:CHCl3) to provide the title compound (98 mg, 40%) as off white solid.

Workup

  1. customOn completion, the reaction mixture was quenched
  2. additionby adding saturated aq. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted with DCM (3×25 mL)
  4. washThe organic layer was washed with water (25 mL), brine (25 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, 0.5:9.5 MeOH:CHCl3)

Sources & evidence

ORD record
ord-e3bdee561a854a85a5b1f9f23d5af5f9
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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