N-Hydroxyacetamidine → HCID 66855074, compound

HRID 1970570Notes

Reaction equation

HRID 1970570 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:31](=[N:34]O)([NH2:33])[CH3:32]>CN(C=O)C.C(OCC)(=O)C>[CH2:12]([O:11][C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]1[O:5][N:34]=[C:31]([CH3:32])[N:33]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 30926N-HydroxyacetamidineHCID 682631,1'-Carbonyldiimidazole2×HCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 66855074HCID 66855074, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 122 mg Z-Pro-OH in 4 ml DMF was added a solution of 325 mg 1,1′-carbonyldiimidazole in 5 ml DMF and the solution was stirred for 30 minutes at RT before a solution of 148 mg acetamide oxime in 3 ml DMF was added. The reaction mixture was stirred for 12 h before 325 mg 1,1′-carbonyldiimidazole were added and the mixture stirred at 115° C. for 5 h. Then, the reaction mixture was diluted with ethyl acetate and washed with aqueous LiCl (4% w/w), saturated aqueous NaHCO3 and 0.1 M HCl. The crude product obtained after evaporation of the solvent was used in the next reaction step without further purification. Yield: 337 mg.

Workup

  1. additionwas added
  2. additionwere added
  3. washwashed with aqueous LiCl (4% w/w), saturated aqueous NaHCO3 and 0.1 M HCl

Sources & evidence

ORD record
ord-b5444398bf3a4fef8573bf76607ef62b
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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