Tetrahydrofuran → HCID 178500291, compound

HRID 1195154Notes

Reaction equation

HRID 1195154 reaction equation
[CH2:1]1COCC1.[C:6]([N:16]=[C:17]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(N1C=CN=C1)(N1C=CN=C1)=O>CO>[CH3:1][O:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:17]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])=[N:16][C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 178525441HCID 178525441, compound

Product 1

HCID 178500291HCID 178500291, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a THF (300 mL) solution of compound 31 (50.8 g, 0.12 mol) was added carbonyldiimidazole (21.4 g, 0.132 mol). The resultant suspension was stirred for 1 h at room temperature. Methanol (75 mL) was added, followed by an additional stirring of the solution for 19 h. The solution was concentrated, and the residue was partitioned between water and ether. The organic phase was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (Et2O:hexane/1:1) to afford 22.8 g (42%) of the title compound.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between water and ether
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (Et2O:hexane/1:1)

Sources & evidence

ORD record
ord-b16fa27da8a3455ba3d8ed11fc867095
Source dataset
uspto-grants-1992_05
Patent number
US05110812

Reaction notes

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