1,1'-Carbonyldiimidazole → HCID 66855550, compound

HRID 1970586Notes

Reaction equation

HRID 1970586 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.O[NH:32][C:33]([CH:35]1[CH2:37][CH2:36]1)=[NH:34]>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:33]([CH:35]2[CH2:37][CH2:36]2)[N:32]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 101987Benzyloxycarbonyl-L-prolineHCID 178513214HCID 178513214, compound

Product 1

HCID 66855550HCID 66855550, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 500 mg Z-Pro-OH in 6 ml DMF was added a solution of 325 mg 1,1′-carbonyldiimidazole in 2 ml DMF. After stirring for 30 minutes a solution of 201 mg N-Hydroxy-cyclopropanecarboxamidine in 2 ml DMF was added and the solution stirred for 12 h at room temperature until LCMS showed complete conversion to the intermediate O-acyl amide oxime. Further 325 mg CDI were added and the mixture stirred at 115° C. for 5 h. It was diluted with ethyl acetate and extracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated to furnish the crude product as colorless oil. Yield: 228 mg.

Workup

  1. additionwas added
  2. stirringthe mixture stirred at 115° C. for 5 h
  3. extractionextracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and 0.1 M HCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b90ad0b69918400bae3eb09a91ef27bc
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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