Tetrahydrofuran → HCID 69314527, compound

HRID 271530Notes

Reaction equation

HRID 271530 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[O:14][C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[C:20](=NO)[CH2:19][CH2:18]4)=[C:12]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH:11]=2)[CH2:6][CH2:5]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:50]1CCCC1>O>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[O:14][C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:50])[CH2:19][CH2:18]4)=[C:12]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 136341915HCID 136341915, compound

Product 1

HCID 69314527HCID 69314527, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of Step 1 (0.135 g, 0.26 mmol) in dry tetrahydrofuran (5 ml) was cooled to 0° C. and treated dropwise with tetrabutylammonium fluoride (1.0M solution in tetrahydrofuran, 0.078 ml, 0.78 mmol) and allowed to warm to room temperature. After stirring for 2 hours, the reaction mixture was diluted with water, extracted with dichloromethane. The organic layer was then washed with saturated aqueous brine, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95) to afford the title compound (0.027 g, 26%); MS(ES+) m/e 403 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was then washed with saturated aqueous brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95)

Sources & evidence

ORD record
ord-39e32906fc1f40b2b35166dbb29c18b2
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

Loading…