Ethyl Acetate → HCID 19071138, compound

HRID 1955616Notes

Reaction equation

HRID 1955616 reaction equation
O=C1O[N:5]=[C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]3[CH2:19][CH:18]([CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:23][CH2:22]4)[O:17][C:16]3=[O:32])[CH2:9][CH2:8]2)[NH:3]1.N1(CCC(OC)=O)CCNCC1.O=C1ON=C(N2CCN(CCN3CC(CS(C)(=O)=O)OC3=O)CC2)N1.C(OCC)(=O)C>CO>[C:4]([N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][N:15]2[CH2:19][CH:18]([CH2:20][N:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:25][CH2:26]3)[O:17][C:16]2=[O:32])[CH2:11][CH2:12]1)(=[NH:3])[NH2:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15343154Methyl 3-(piperazin-1-yl)propanoateHCID 136351310HCID 136351310, compoundHCID 136482112HCID 136482112, compound

Product 1

HCID 19071138HCID 19071138, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.13 g of 3-[2-(1-(5-oxo-1,2,4-oxadiazolin-3-yl)-4-piperazinyl)ethyl]-5-[4-(2-carboxyethyl)piperazino]methyloxazolidin-2-one [obtainable according to Ex. 1 by reaction of methyl 3-piperazinopropanoate with 3-[2-(1-(5-oxo-1,2,4-oxadiazolin-3-yl)-4-piperazinyl)ethyl]-5-methanesulfonylmethyloxazolidin-2-one and subsequent hydrolysis of the product] are dissolved in 50 ml of methanol and hydrogenated on Raney Nickel. The reaction mixture is then filtered and the filtrate is concentrated in vacuo. The product obtained is treated with 20 ml of ethyl acetate in the presence of heat and filtered off with suction after cooling. 3-[2-(1-Amidino-4-piperazinyl)ethyl]-5-[4-(2-carboxyethyl)piperazino]methyloxazolidin-2-one is obtained.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe product obtained
  4. temperatureof heat
  5. filtrationfiltered off with suction
  6. temperatureafter cooling

Sources & evidence

ORD record
ord-6aeafc7daa3e4b2bbb30bbe44f5a3dd1
Source dataset
uspto-grants-1998_07
Patent number
US05776937

Reaction notes

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