Tetrahydrofuran → HCID 18989337, compound

HRID 2395814Notes

Reaction equation

HRID 2395814 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14]N1C(CCC=O)C(=O)OC1)(=[O:13])=[O:12].Cl.[C:26]([C:28]1[CH:44]=[CH:43][C:31]([CH2:32][C@@H:33]([C:35]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:36])[NH2:34])=[CH:30][CH:29]=1)#[N:27].[C:45]([O-:48])(=O)[CH3:46].[Na+].C([BH3-])#N.[Na+].[CH2:54]1[CH2:58]OC[CH2:55]1>C(Cl)Cl.CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][CH:46]1[CH2:58][CH2:54][CH2:55][N:34]([CH:33]([C:35]([N:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)=[O:36])[CH2:32][C:31]2[CH:30]=[CH:29][C:28]([C:26]#[N:27])=[CH:44][CH:43]=2)[C:45]1=[O:48])(=[O:12])=[O:13]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18989310HCID 18989310, compoundHCID 22858564HCID 22858564, compound

Product 1

HCID 18989337HCID 18989337, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12 °C

Procedure

2.5 g (~7.5 mmol) of 3-[3-(2-naphthalenesulfonylamino)oxazolidin-5-on-4-yl]propanal, as crude product, in 15 ml of methylene chloride, 2.2 g (7.5 mmol) of p-cyanophenylalaninylpiperidine hydrochloride in 15 ml of methylene chloride and 1.2 g (14.6 mmol) of sodium acetate were successively added to 7.5 g of freshly activated molecular sieves (4 Å) in 30 ml of methanol. The mixture was cooled to about 12° C. and then 0.9 g (14.3 mmol) of sodium cyanoborohydride dissolved in 20 ml of THF was added dropwise over the course of 35 min, and the mixture was stirred at room temperature for 3 h. The solids were then removed by filtration and washed with methylene chloride, the collected filtrates were evaporated under reduced pressure, the residue was taken up in ethyl acetate, and the solution was washed with dilute aqueous sulfamic acid solution (pH 1) and five times with saturated brine, dried over magnesium sulfate and evaporated under reduced pressure. Chromatography on silica gel (0.063-0.200 mm/eluent methylene chloride/methanol) resulted in 3.5 g (85% of theory over 3 stages) of pure 3-(2-naphthalenesulfonylamino)-1-[2-(4-cyanophenyl)-1-piperidinocarbonylethyl]-2-piperidinone.

Workup

  1. additionwas added dropwise over the course of 35 min
  2. customThe solids were then removed by filtration
  3. washwashed with methylene chloride
  4. customthe collected filtrates were evaporated under reduced pressure
  5. washthe solution was washed with dilute aqueous sulfamic acid solution (pH 1) and five times with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customChromatography on silica gel (0.063-0.200 mm/eluent methylene chloride/methanol) resulted in 3.5 g (85% of theory over 3 stages) of pure 3-(2-naphthalenesulfonylamino)-1-[2-(4-cyanophenyl)-1-piperidinocarbonylethyl]-2-piperidinone

Sources & evidence

ORD record
ord-b9401f49b14c46149148ddf4de485a99
Source dataset
uspto-grants-1996_02
Patent number
US05489583

Reaction notes

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