Acetic Acid → HCID 86760451, compound

HRID 459067Notes

Reaction equation

HRID 459067 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(O)(=O)C.[CH2:23]([O:25][C:26](=[O:78])[CH2:27][CH2:28][CH2:29][C:30](=[O:77])[CH2:31][C@H:32]([OH:76])/[CH:33]=[CH:34]\[C@H:35]([CH3:75])[C@H:36]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[C@@H:37]([CH3:66])/[CH:38]=[C:39](/[CH3:65])\[CH2:40][C@H:41]([CH3:64])[C@@H:42]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[C@H:43]([CH3:55])[C@@H:44]([O:51][C:52]([NH2:54])=[O:53])[C@@H:45]([CH3:50])/[CH:46]=[CH:47]\[CH:48]=[CH2:49])[CH3:24]>C(#N)C>[CH2:23]([O:25][C:26](=[O:78])[CH2:27][CH2:28][CH2:29][C@@H:30]([OH:77])[CH2:31][C@H:32]([OH:76])/[CH:33]=[CH:34]\[C@H:35]([CH3:75])[C@H:36]([O:67][Si:68]([C:71]([CH3:72])([CH3:73])[CH3:74])([CH3:69])[CH3:70])[C@@H:37]([CH3:66])/[CH:38]=[C:39](/[CH3:65])\[CH2:40][C@H:41]([CH3:64])[C@@H:42]([O:56][Si:57]([C:60]([CH3:61])([CH3:62])[CH3:63])([CH3:58])[CH3:59])[C@H:43]([CH3:55])[C@@H:44]([O:51][C:52]([NH2:54])=[O:53])[C@@H:45]([CH3:50])/[CH:46]=[CH:47]\[CH:48]=[CH2:49])[CH3:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 86760452HCID 86760452, compound

Product 1

HCID 86760451HCID 86760451, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 250 mg (0.95 mmol) of tetramethylammonium triacetoxyborohydride in 0.52 mL of anhydrous acetonitrile is added 0.52 mL of anhydrous acetic acid and the mixture is stirred at ambient temperature for 30 minutes. The mixture is cooled to −29° C., and a solution of 50 mg (0.453 mmol) of (7S,8Z,10S,11S,12S,13Z,16S,17R,18R,19S,20S,21Z)-19-[(aminocarbonyl)oxy]-11,17-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-10,12,14,16,18,20-hexamethyl-5-oxo-8,13,21,23-tetracosatetraenoic acid ethyl ester in 0.5 mL anhydrous acetonitrile is added. The mixture is stirred at −29° C. for 18 hours. The reaction is quenched with 1 mL of 0.5N aqueous sodium potassium tartrate and the mixture is allowed to warm slowly to ambient temperature. The mixture is diluted with CH2Cl2 and washed with aqueous saturated NaHCO3. The aqueous layer is back extracted with CH2Cl2 four times. The combined organic layers are washed with brine, dried with Na2SO4 and concentrated in vacuo to give the crude product as a white solid (50 mg, 99%). m/z (ESI+) 846 (100 (M+Na+)).

Workup

  1. temperatureThe mixture is cooled to −29° C.
  2. stirringThe mixture is stirred at −29° C. for 18 hours
  3. customThe reaction is quenched with 1 mL of 0.5N aqueous sodium potassium tartrate
  4. temperatureto warm slowly to ambient temperature
  5. additionThe mixture is diluted with CH2Cl2
  6. washwashed with aqueous saturated NaHCO3
  7. extractionThe aqueous layer is back extracted with CH2Cl2 four times
  8. washThe combined organic layers are washed with brine
  9. dry with materialdried with Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a93f236474fe4ce5a1d8fe9eaac7bf1f
Source dataset
uspto-grants-2007_03
Patent number
US07192980B2

Reaction notes

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