Tetrahydrofuran → HCID 58032200, compound

HRID 2167257Notes

Reaction equation

HRID 2167257 reaction equation
C(N(CC)CC)C.C1C[O:11][CH2:10]C1.[C:13]([N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:26]([NH:28][NH2:29])=[O:27])=[CH:23][CH:24]=2)[CH:19]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH2:18][CH:17]1[CH3:38])(=[O:15])[CH3:14]>O>[C:13]([N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:26]3[O:27][C:10](=[O:11])[NH:29][N:28]=3)=[CH:23][CH:24]=2)[CH:19]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:18][CH:17]1[CH3:38])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 46932456HCID 46932456, compound

Product 1

HCID 58032200HCID 58032200, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (744 μL, 534 μmol) was added to a THF (10 mL) solution of compound 115 (100 mg, 267 μmol) at room temperature, and 1,1′-carbodiimidazole (64.9 mg, 400 μmol) was further added thereto. The resulting mixture was stirred for 3 days at the same temperature. Water was added to the reaction liquid, and the mixture was extracted with chloroform. Subsequently, the organic layer was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (hexane:ethyl acetate=1:1-÷ 1:2), and thus 94.8 mg (89%) of the title compound was obtained as a pale yellow amorphous substance (cis:trans=3:1).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washSubsequently, the organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-370f6d2d001f40d19de2c68153b544c2
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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