Trifluoroacetic acid → HCID 56607844, compound

HRID 375724Notes

Reaction equation

HRID 375724 reaction equation
FC(F)(F)C(O)=O.[Si:8]([O:15][C:16]1[CH:17]=[C:18]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[C:19]2[CH2:30][S:29][CH2:28][C@@H:27]([C:31]([O:33][CH3:34])=[O:32])[NH:26][C:25](=[O:35])[C@@H:24]([NH:36]C(OC(C)(C)C)=O)[CH2:23][O:22][C:21](=[O:44])[C:20]=2[C:45]=1[CH3:46])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>>[NH2:36][C@H:24]1[CH2:23][O:22][C:21](=[O:44])[C:20]2[C:45]([CH3:46])=[C:16]([O:15][Si:8]([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:10])[CH3:9])[CH:17]=[C:18]([O:47][Si:48]([C:51]([CH3:52])([CH3:53])[CH3:54])([CH3:49])[CH3:50])[C:19]=2[CH2:30][S:29][CH2:28][C@@H:27]([C:31]([O:33][CH3:34])=[O:32])[NH:26][C:25]1=[O:35]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10996150HCID 10996150, compound

Product 1

HCID 56607844HCID 56607844, compoundYield 77.2%

Conditions

Temperature
0 °C

Procedure

To 15 ml of trifluoroacetic acid, cooled to 0° C., were added 1.07 g of tert-butyl (4R, 7S)-12,14-bis (tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-4-methoxycarbonyl11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7carbamate. The solution was stirred at 0° C. for 30 minutes, and then the solvent was evaporated in vacuo. The residue was dissolved in 50 ml of ethyl acetate, and the solution was washed successively with saturated sodium carbonate solution and with brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. Crystallization of the residual material from hexane at -20° C. yielded 0.71 g of methyl (4R, 7S)-7-amino-12,14-bis-(tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-11-methyl-6,10-dioxo-9,2,5-benzooxathiaazacyclododecine-4-carboxylate as white crystals of m.p. 135°-141° C. (dec.).

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  3. washthe solution was washed successively with saturated sodium carbonate solution and with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customCrystallization of the residual material from hexane at -20° C.

Sources & evidence

ORD record
ord-fee708ae60c64fa88ad76274fbe492fe
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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