1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86700688, compound

HRID 1406870Notes

Reaction equation

HRID 1406870 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[O:19]C(C2CCNCC2)=N[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:31]=[C:32]=[N:33]CCCN(C)C.C1C=CC2N(O)N=NC=2C=1.ONC(N)=N>CN(C=O)C.O>[NH2:33][C:32]1[N:22]=[C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:19][N:31]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 86700689HCID 86700689, compoundHCID 178513189HCID 178513189, compound

Product 1

HCID 86700688HCID 86700688, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,5R)-6-(benzyloxy)-2-(5-(piperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (2.0 g, 7.25 mmol), EDCI (1.53 g, 7.98 mmol) and HOBT (1.08 g, 7.98 mmol) in DMF (15 mL) was stirred at rt for 0.5 h. 1-Hydroxyguanidine (0.653 g, 7.98 mmol) was then added and the reaction mixture was stirred for an additional 0.5 h. The resulting solution was treated under microwave at 100° C. for 1.5 hrs. The mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether) to give (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (1.0 g, 44%). (ESI-MS (EI+, m/z): 316 [M+H]+.

Workup

  1. additionThe resulting solution was treated under microwave at 100° C. for 1.5 hrs
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-d3d85a93c60e4eb29540b4fced52d09e
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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