Acetic Acid → HCID 86759459, compound

HRID 353764Notes

Reaction equation

HRID 353764 reaction equation
[CH3:1][N:2]([CH3:66])[C@H:3]1[CH2:63][C@@H:62]([CH3:64])[O:61][CH:5]([O:6][C@@H:7]2[C@@H:23]([CH3:24])[C:22](=[O:25])[C@@H:21]([CH3:26])[C:20](=[O:27])[O:19][C@H:18]([CH2:28][CH3:29])[C@:17]3([CH2:30][O:31][Si](C(C)(C)C)(C)C)[C@H:13]([N:14]([CH2:40][CH2:41][CH2:42][CH2:43][N:44]4[CH:48]=[C:47]([C:49]5[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=5)[N:46]=[CH:45]4)[C:15](=[O:39])[O:16]3)[C@@H:12]([CH3:55])[C:11](=[O:56])[C@H:10]([CH3:57])[CH2:9][C@:8]2([O:59][CH3:60])[CH3:58])[C@@H:4]1[OH:65].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[CH3:66][N:2]([CH3:1])[C@H:3]1[CH2:63][C@@H:62]([CH3:64])[O:61][CH:5]([O:6][C@@H:7]2[C@@H:23]([CH3:24])[C:22](=[O:25])[C@@H:21]([CH3:26])[C:20](=[O:27])[O:19][C@H:18]([CH2:28][CH3:29])[C@:17]3([CH2:30][OH:31])[C@H:13]([N:14]([CH2:40][CH2:41][CH2:42][CH2:43][N:44]4[CH:48]=[C:47]([C:49]5[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=5)[N:46]=[CH:45]4)[C:15](=[O:39])[O:16]3)[C@@H:12]([CH3:55])[C:11](=[O:56])[C@H:10]([CH3:57])[CH2:9][C@:8]2([O:59][CH3:60])[CH3:58])[C@@H:4]1[OH:65]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86759460HCID 86759460, compound

Product 1

HCID 86759459HCID 86759459, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To (3aR,4R,7R,9R,10R,11R,13 R,15R,15aR)-3a-({[tert-butyl(dimethyl)silyl]-oxy}methyl)-4-ethyl-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-1-[4-(4-pyridin-3-yl-1H-imidazol-1-yl)butyl]tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (1 eq) in tetrahydrofuran was added acetic acid (2 eq) and tetrabutylammonium fluoride/1.0M in tetrahydrofuran (2 eq). After standing for 48 hours, ethyl acetate was added and the solution was washed with NaHCO3(sat.), NaCl(sat.), dried over MgSO4, filtered, and concentrated. Purification by RP HPLC afforded (3aR,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-3a-(hydroxymethyl)-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-1-[4-(4-pyridin-3-yl-1H-imidazol-1-yl)-butyl]tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (48% yield) as a white solid. MH+(828.50).

Workup

  1. washthe solution was washed with NaHCO3(sat.), NaCl(sat.)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by RP HPLC

Sources & evidence

ORD record
ord-6ce76eb9a9ad47228b93324094d758d3
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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