Sodium Bicarbonate → HCID 90947908, compound

HRID 1250124Notes

Reaction equation

HRID 1250124 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C@@H:15]1[C@:19]([Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([OH:20])[C@@H:18]([CH2:38][O:39][C:40]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[O:17][C@H:16]1[N:63]1[C:72]2[N:71]=[CH:70][N:69]=[C:67]([NH2:68])[C:66]=2[N:65]=[CH:64]1)=[O:7])#[N:2].[C:73](C1NN=NN=1)(=[O:80])[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1.CC(C)=O.C(Cl)Cl.C(=O)(O)[O-].[Na+]>CC#N.CCOC(C)=O.O>[C:73]([NH:68][C:67]1[C:66]2[N:65]=[CH:64][N:63]([C:72]=2[N:71]=[CH:70][N:69]=1)[C@@H:16]1[O:17][C@H:18]([CH2:38][O:39][C:40]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[C@@:19]([Si:21]([C:34]([CH3:35])([CH3:36])[CH3:37])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([OH:20])[C@H:15]1[O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])=[O:7])(=[O:80])[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 20716773HCID 20716773, compoundHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 178519510HCID 178519510, compound

Product 1

HCID 90947908HCID 90947908, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 54 (0.25 g, 0.25 mmol) and benzoyl-tetrazole (0.09 g, 0.50 mmol) in anhydrous CH3CN (0.5 mL) was stirred in a preheated bath at 65° C. for 1.5 h. After this time, the TLC (10% CH3COCH3/CH2Cl2) that the reaction was complete. The reaction mixture was cooled to room temperature and taken up in EtOAc (30 mL) ,washed with aq saturated sodium bicarbonate solution (2×15 mL) and water (15 mL) dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using 10% CH3COCH3/CH2Cl2 as the eluent and the appropriate fractions were combined and concentrated to give a colorless foam, yield (0.105 g, 50%).

Workup

  1. dry with materialdried over anhydrous Na2SO4
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel using 10% CH3COCH3/CH2Cl2 as the eluent
  4. concentrationconcentrated
  5. customto give a colorless foam
  6. customyield (0.105 g, 50%)

Sources & evidence

ORD record
ord-dbbc4745f9bd46949d30a5c504af8814
Source dataset
uspto-grants-2002_01
Patent number
US06335434B1

Reaction notes

Loading…