HCID 20716773, compound → HCID 90947908, compound

HRID 983182Notes

Reaction equation

HRID 983182 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>CCOC(C)=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

5

Reactant 3

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

Product 1

HCID 90947908HCID 90947908, compound

Reagents, catalysts & solvents 1

HCID 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 CH2CN (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%). 1H NMR (CDCl3) d 11.21 (s, 1H), 8.58 and 8.56 (2s, 2H), 8.04 (d, 2H, J=7.3 Hz), 7.70-7.09 (m, 22H), 6.78 (d, 4H, J=8.0 Hz), 6.23 (d, 1H, J=4.6 Hz), 4.73-4.69 (m, 1H), 4.44-4.39 (m, 1H), 4.30-4.20 (m, 1H), 4.10 (t, 2H, J=6.1 Hz), 3.71 (s, 6H), 3.25-2.79 (m, 8H), 1.39-1.02 (m, 15H).

Workup

  1. washwashed with aq saturated sodium bicarbonate solution (2×15 mL) and water (15 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. customSolvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel using 10% CH3COCH3/CH2Cl2 as the eluent
  5. concentrationconcentrated
  6. customto give a colorless foam
  7. customyield (0.105 g, 50%)

Sources & evidence

ORD record
ord-482763ca201a4832a9947c8071261013
Source dataset
uspto-grants-2005_03
Patent number
US06861514B2

Reaction notes

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