Formic Acid → HCID 86622678, compound

HRID 1946622Notes

Reaction equation

HRID 1946622 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([O:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:34](=[O:35])[C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[O:31][C:30]2[CH:40]=[CH:41][CH:42]=[CH:43][C:29]1=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)=O>C1COCC1.C(OCC)(=O)C>[CH2:13]([O:20][N:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:34](=[O:35])[C:33]2[CH2:36][CH2:37][CH:38]=[CH:39][C:32]=2[O:31][C:30]2[CH:40]=[CH:41][CH:42]=[CH:43][C:29]1=2)[CH:1]=[O:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 86622679HCID 86622679, compound

Product 1

HCID 86622678HCID 86622678, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1,1′-Carbonyldiimidazole (1.26 g, 7.8 mmol) was dissolved in THF (15 mL) and the mixture was cooled at 0° C. Title compound 402 (0.646 g, 1.56 mmol) and formic acid in solution in THF (5 mL) was added. The reaction mixture was stirred at room temperature for 3 hours then diluted in ethyl acetate. The organic phase was washed with a saturated aqueous solution of bicarbonate, water and brine, then evaporated. The residue was purified by flash chromatography (30-50% ethyl acetate in hexanes) to afford title compound 403 (348 mg, 50%) as a colorless oil. MS (m/z): 445.2 (M+H).

Workup

  1. washThe organic phase was washed with a saturated aqueous solution of bicarbonate, water and brine
  2. customevaporated
  3. customThe residue was purified by flash chromatography (30-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c9db54d20728414eb1e785ccefb81c29
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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