1,1'-Carbonyldiimidazole → HCID 19080431, compound

HRID 964461Notes

Reaction equation

HRID 964461 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=[CH:12][C:11]=2[CH2:19][C:20]([OH:22])=O)=[C:7]([CH2:25][CH2:26][CH3:27])[CH:6]=1)([O:3][CH3:4])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[C:40]([C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH2:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1)([CH3:43])([CH3:42])[CH3:41].C1CCN2C(=NCCC2)CC1>C1COCC1>[C:40]([C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH:53][C:20](=[O:22])[CH2:19][C:11]2[CH:12]=[CH:13][C:14]3[O:18][CH2:17][O:16][C:15]=3[C:10]=2[O:9][C:8]2[CH:23]=[CH:24][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:6][C:7]=2[CH2:25][CH2:26][CH3:27])(=[O:51])=[O:52])=[CH:46][CH:45]=1)([CH3:43])([CH3:41])[CH3:42]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2228724-tert-ButylbenzenesulfonamideHCID 19080418HCID 19080418, compound

Product 1

HCID 19080431HCID 19080431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To the product of Step A (57.2 mg, 0.154 mmol) in dry THF (0.75 mL) was added CDI (76.0 mg, 0.469 mmol) and the reaction heated to 50° C. for 2.5 hr. To this solution was added a solution of p-t-butylphenyl-sulfonamide (131.7 mg, 0.618 mmol) and DBU (92.1 μL, 0.594 mmol) in dry THF (0.75 mL). The reaction continued to be stirred at 50° C. monitoring by thin layer chromatography until all of the mono-acid was consumed (approx. 3 hr). The reaction was concentrated in vacuo and the residue was taken up in 50:50/Et2O:EtOAc. The organic phase was washed with 10% citric acid (2×), water and brine then dried over MgSO4, filtered and the solvent removed. Purification was accomplished by radial chromatography eluting with 3:2/Hex:EtOAc. Yield=74.3 mg (0.131 mmol, 85%) rf=0.32 (80:10:1/CHCl3 :MeOH:NH4OH) FAB mass spectrum, m/e 590.0 (M+Na calculated for C30H33 NSO8 590). See Drummond, J. T.; Johnson, G. Tetrahedron Lett., 1988, 29, 1653.

Workup

  1. customwas consumed (approx. 3 hr)
  2. concentrationThe reaction was concentrated in vacuo
  3. washThe organic phase was washed with 10% citric acid (2×), water and brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. customPurification
  8. washeluting with 3:2/Hex

Sources & evidence

ORD record
ord-4727e36124e54367a0bcf4fcd98526d5
Source dataset
uspto-grants-1998_06
Patent number
US05767310

Reaction notes

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