HCID 12196378, compound → HCID 178511308, compound

HRID 1089265Notes

Reaction equation

HRID 1089265 reaction equation
Cl.[NH2:2][CH:3]([C:7]#[N:8])[C:4]([NH2:6])=[O:5].[CH2:9]([O:16][CH2:17][C@H:18]([O:29][N:30]=[CH:31]N(C)C)[CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[CH2:9]([O:16][CH2:17][CH:18]([O:29][N:30]=[CH:31][NH:2][C@H:3]([C:7]#[N:8])[C:4]([NH2:6])=[O:5])[CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 12196378HCID 12196378, compoundHCID 54124514HCID 54124514, compound

Product 1

HCID 178511308HCID 178511308, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-2-cyanoacetamide hydrochloride (0.19 g, 1.4 mmol) and (R)-N'-(1,4-dibenzyloxybut-2-oxy)-N,N-dimethylmethanimidamide (0.5 g, 1.4 mmol) in methanol (1.5 ml) was stirred at room temperature for 20 hours. The solvent was removed under reduced pressure and the residue treated with ethyl acetate (20 ml) and brine (0.05 ml). The organic solution was decanted and dried (MgSO4). The solvent was removed under reduced pressure and the residual oil extracted with hexane (3×10 ml). The hexane was decanted and the residual oil was dissolved in warm chloroform (3 ml) and treated with hexane (20 ml). After refrigeration (-18° C.) for 1 hour, the organic solution was decanted and the insoluble oil dried under vacuum to give (R)-2-[N-(1,4-dibenzyloxy-but-2-oxy)iminomethyl]amino-2-cyanoacetamide (0.37 g, 74%); IR: υmax (film) 3340, 3190, 3090, 3060, 3030, 2950, 2920, 2860, 2800, 1700, 1660, 1600, 1495, 1455, 1375, 1310, 1240, 1215, 1145, 1125, 1025, 985, 945, 905, 740, 700 cm-1 ; 1H NMR: δH [(CD3)2SO] 1.87 (2H, m, CH2), 3.54 (4H, m, 2×CH2), 4.05 (0.12H, m, CH), 4.13 (0.88H, m, CH), 4.45 (4H, m, 2×CH2), 5.07 (0.13H, d, J=8 Hz, CH), 5.26 (0.87H, d, J=8 Hz, CH), 6.80 (1H, d, J=10.5 Hz, CH), 6.92 (1H, dd, J=10.5 and 8 Hz, NH), 7.2-7.8 (12H, m, 2×C6H5 plus D2O exchangeable NH2); m/z (NH3CI) M+ 411. Found: C, 61.83; H, 6.50; N, 13.32%. C22H26N4O4. H2O requires: C, 61.67; H, 6.59; N, 13.08%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue treated with ethyl acetate (20 ml) and brine (0.05 ml)
  3. customThe organic solution was decanted
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. extractionthe residual oil extracted with hexane (3×10 ml)
  7. customThe hexane was decanted
  8. dissolutionthe residual oil was dissolved in warm chloroform (3 ml)
  9. additiontreated with hexane (20 ml)
  10. customthe organic solution was decanted
  11. customthe insoluble oil dried under vacuum

Sources & evidence

ORD record
ord-471ce10cf25a427db4c7181a950c28e5
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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