Sodium Bicarbonate → HCID 86623505, compound

HRID 503027Notes

Reaction equation

HRID 503027 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]1([C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:16]2[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=[N:19][N:18]=[N:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:39]([O:47][C@@H:48]1[CH2:56][C@@H:51]2[O:52][C:53](=[O:55])[CH2:54][C@@H:50]2[C@H:49]1/[CH:57]=[CH:58]/[C@@H:59]([O:66][Si:67]([C:80]([CH3:83])([CH3:82])[CH3:81])([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)[CH:60]([CH3:65])[CH2:61][CH2:62][CH2:63][CH3:64])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[C:39]([O:47][C@@H:48]1[CH2:56][C@@H:51]2[O:52][C:53]([CH:24]([CH2:23][CH2:22][CH2:21][C:20]3[N:16]([C:15]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:17]=[N:18][N:19]=3)[C:25]#[N:26])([OH:55])[CH2:54][C@@H:50]2[C@H:49]1/[CH:57]=[CH:58]/[C@@H:59]([O:66][Si:67]([C:80]([CH3:82])([CH3:81])[CH3:83])([C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1)[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)[CH:60]([CH3:65])[CH2:61][CH2:62][CH2:63][CH3:64])(=[O:46])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 68460237HCID 68460237, compoundHCID 68461570HCID 68461570, compound

Product 1

HCID 86623505HCID 86623505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithium diisopropylamide (13.4 mL, 26.8 mmol, 2M solution) in THF (170 mL) was cooled to −78° C. as a solution of 1-(triphenylmethyl)-1H-tetrazole-5-pentanenitrile (10.55 g, 26.8 mmol) in THF (30 mL) was added slowly. The reaction was allowed to warm to ambient temperature 30 min, before cooling to −78° C. The reaction was stirred as a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)-4-[(1E,3S)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-one (3.3 g, 5.4 mmol) in THF (50 mL) was added slowly. The reaction was warmed to room temperature and stirred for 16 h. The reaction was treated with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried and concentrated. Purification by normal phase chromatography eluting with a gradient of ethyl acetate in hexane afforded α-[(3aR,4R,5R,6aS)-5-(benzoyloxy)-4-[(1E,3S)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methyl-1-octenyl]hexahydro-2-hydroxy-2H-cyclopenta[b]furan-2-yl]-1-(triphenylmethyl)-1H-tetrazole-5-pentanenitrile.

Workup

  1. additionwas added slowly
  2. temperaturebefore cooling to −78° C
  3. additionwas added slowly
  4. temperatureThe reaction was warmed to room temperature
  5. extractionextracted with ethyl acetate
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. customPurification by normal phase chromatography
  9. washeluting with a gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-aceedc0c0ae9489491418223c226834c
Source dataset
uspto-grants-2010_08
Patent number
US07776896B2

Reaction notes

Loading…