Acetic Acid → HCID 44366862, compound

HRID 2260889Notes

Reaction equation

HRID 2260889 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[S:24][CH:23]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([NH2:35])=[N:29][C:30]=3[NH2:34])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C(OCC)C>[CH:23]1([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([NH2:35])=[N:29][C:30]=3[NH2:34])[S:24][C@H:20]([CH2:19][OH:18])[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 22844873HCID 22844873, compound

Product 1

HCID 44366862HCID 44366862, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 16 (50 mg, 0.1 mmol), acetic acid (7 μL, 0.12 mmol), and 0.17 mL of 1M tetrabutylammonium fluoride in THF (0.17 mmol) was stirred in 10 mL tetrahydrofuran overnight. Water (2 mL) and 15 mL ethyl ether were added followed by stirring for 5 minutes. The organic phase was extracted with 2 mL water and then the combined aqueous solution was washed with 15 mL ethyl ether. The aqueous extract was concentrated in vacuo to 1 mL and then applied to a 4-mL Dowex 1×4 100-200 (-3OH) column to remove tetrabutylammonium salts by eluting with water followed by 20% aqueous methanol. The solvent was removed in vacuo and the product was recrystallized from ethanol/ethyl acetate to afford 19.5 mg (54%) of 17; mp. 187°-90° C. dec; FAB MS 267 (M+H)+ ; 1H NMR (DMSO-d6) δ 8.0 (s, 1, H-8), 6.68 (br, s, 2, NH2), 5.95 (m, 1, I'-H), 5.71 (brs, 2, NH2), 5.22 (m, 1, 5'-OH), 3.73 (m, 1, 5'-H), 3.57 (m, 2, 4'-H, 5'-H), 2.4 (m, 1, 2'-H), 2.32 (m, 1, 2'-H), 2.12 (m, 1, 3'-H), 1.98 (m, 1, 3'-H).

Workup

  1. extractionThe organic phase was extracted with 2 mL water
  2. washthe combined aqueous solution was washed with 15 mL ethyl ether
  3. extractionThe aqueous extract
  4. concentrationwas concentrated in vacuo to 1 mL
  5. customto remove tetrabutylammonium salts
  6. washby eluting with water
  7. customThe solvent was removed in vacuo
  8. customthe product was recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-2b15bd030f194f75b6c9f4ca14224b7c
Source dataset
uspto-grants-1995_12
Patent number
US05478928

Reaction notes

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