Hydrochloric Acid → HCID 67268813, compound

HRID 602732Notes

Reaction equation

HRID 602732 reaction equation
[O-]CC.[Na+].[C:5]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([N:23]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][C:25]#[C:26][CH3:27])=[N:20][C:21]#[N:22])[CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl>C(O)C>[NH2:22][C:21]1[N:20]=[C:19]([N:15]2[CH2:16][CH2:17][CH2:18][CH:13]([NH:12][C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:11])[CH2:14]2)[N:23]([CH2:24][C:25]#[C:26][CH3:27])[C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 86602513HCID 86602513, compound

Product 1

HCID 67268813HCID 67268813, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g sodium ethoxide are added to a solution of 12.5 g (approx. 90%) 3-tert-butoxycarbonylamino-N-(ethoxycarbonylmethyl)-N-(but-2-ynyl)-N′-cyano-piperidine-1-carboxamidine in 100 ml dry ethanol. The reaction solution is stirred for 3 h at ambient temperature and then neutralised with 1 M hydrochloric acid. The solvent is removed, water is added and the mixture is extracted with ethyl acetate. The organic extracts are dried over sodium sulphate, the solvent is removed, and the residue is purified on silica (cyclohexane/ethyl acetate 3:1->1:5).

Workup

  1. customThe solvent is removed
  2. additionwater is added
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe organic extracts are dried over sodium sulphate
  5. customthe solvent is removed
  6. customthe residue is purified on silica (cyclohexane/ethyl acetate 3:1->1:5)

Sources & evidence

ORD record
ord-5f550d5f6997451fa8e7668a37a44cae
Source dataset
uspto-grants-2011_03
Patent number
US07906539B2

Reaction notes

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