Tetrahydrofuran → HCID 178500410, compound

HRID 1728471Notes

Reaction equation

HRID 1728471 reaction equation
[CH2:1]1COCC1.[C:6]([N:16]=[C:17]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([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:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:17]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])=[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 178525456HCID 178525456, compound

Product 1

HCID 178500410HCID 178500410, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. THF (700 mL) solution of compound 1 (133 g, 0.3 mol) was added carbonyldiimidazole (55.3 g, 0.34 mol). After the addition was complete, the resultant solution was allowed to warm to room temperature and stirred for 45 min. Anhydrous methanol (100 mL) was added. The solution was stirred for 16 h and concentrated. The residue was triturated with ether (400 mL). The supernatant was separated. The process was repeated with two more portions of ether (2×200 mL). The ether phases were combined, washed with H2O, dried (MgSO4), and concentrated. The residue was purified by silica gel chromatography (Et2O:hexane/1:1) to afford 130 g (95%) of the title product, mp 36°-39° C.

Workup

  1. customTo a 0° C
  2. additionAfter the addition
  3. stirringThe solution was stirred for 16 h
  4. concentrationconcentrated
  5. customThe residue was triturated with ether (400 mL)
  6. customThe supernatant was separated
  7. washwashed with H2O
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (Et2O:hexane/1:1)

Sources & evidence

ORD record
ord-3bf9a90023af4b98958fd6fae0e76976
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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